Multicomponent Heterocyclizations with Controlled Selectivity. Reactions of Carbonyls with...
337
Transcript of Multicomponent Heterocyclizations with Controlled Selectivity. Reactions of Carbonyls with...
1
........................................................................... 5
.................................................................................................................. 7
1
: ................................... 11
1.1.
- .................................. 12
1.2.
........................................................................... 17
1.3. -
............................................................................................. 34
1.3.1. ........................................................ 35
1.3.2. ........................................................... 44
1.3.3. ......................................... 49
1.3.4. 1,2- . ..... 73
2
................. 81
2.1. ................. 82
2.1.1. .................................................. 82
2.1.2. ............................................. 93
2.2.
................................................................................................... 101
2.3. ..................................................... 108
3
-
.......................................................................................................... 114
2
3.1. 1,3-
5- ................................................................ 115
3.1.1. [3,4-b] -5-
[5,1-b] -8- ............................................................... 115
3.1.2. 5-
.................................................... 120
3.1.3. 5- -N- -4- ..................... 126
3.1.5. N-
................................................................... 130
3.2. .............................................................. 135
3.3. 6- ........................................................................ 141
3.3.1.
1,3- ........................................................................................... 141
3.3.2.
............................................................................................... 143
3.4. ...................................................................... 148
4
-
: ,
...................................................................................................... 156
4.1. 1,2,5,6- ................... 157
4.1.1. 1,2,5,6- .. 157
4.1.2. 1,2,5,6- ............................ 167
4.2. - ... 172
4.2.1. -
.................................................................................................... 173
4.2.2. ............. 187
5
............................ 207
5.1. , 2 ............ 207
3
5.2. , 3 ............ 212
5.3. , 4 ............ 217
6
................................................... 226
6.1. ......................................... 226
6.2. ............................. 230
6.3. ...................................... 232
5.2. ..................................... 233
......................................................................................................... 236
........................................................................................................ 240
......................................................................... 241
1.
................................................................................................. 241
2. ..................................................................... 241
3. ....................................................................... 243
........................................................................................... 266
4
5
COSY Corelation spectroscopy (
)
DFT Density functional theory (
)
DPPH 2,2-Diphenyl-1-picrylhydrazyl (2,2- -1-
)
EXSY Exchange spectroscopy ( )
HMBC Heteronuclear multiple bond correlation (
2-3 )
HSQC Heteronuclear single quantum coherence (
)
MW Microwave (
)
NOESY Nuclear Overhauser enhancement spectroscopy
( )
ROESY Rotating frame Overhauser effect spectroscopy (
)
TOCSY Total correlation spectroscopy (
)
US Ultrasonication ( )
( -d6) ( -
)
6
-
(1 , 13 , 1D,
2D)
( ,
, , )
7
,
, ,
, .
«
», ,
, ,
,
. ,
,
, ,
« ».
, ,
, ,
,
, ,
.
-
,
,
.
,
. ,
,
,
, ,
,
.
8
,
, ,
, ,
.
, ,
-, -
.1
,
« »
.
,
.
,
, ,
,
1 ,
. , , , ( , R R1),
( A-B C-D), , 1,3- –
( A-C B-D).
9
.
, , -
3- -1,2,4- , 5- , 5-
, 6- , , 1,2- ,
.
, , ,
,
.
, ,
, ,
,
.
,
,
,
,
, , , .
,
: ( )
; ( )
; ( )
.
10
, ,
,
,
.
, ,
50 – 60 ° .
,
, ,
,
. ,
, ,
.
* * *
. . , . . , . . ,
. . , . . , . . , . . , . . ,
. . , . . , . . , . . , . . ,
. . , . . , . . , . . , . .
.
11
1
:
( , )
( + + ),
,
[1] ,
,
,
.
: ( + )+ , ( + )+ ( + )+ .
,
,
.
,
, ,
, .
, CH- ,
( )
( 1.1).
1.1
12
( I)
- -
( II), ( III) ( IV).
,
-
, , ,
. ,
( ., , [2-11]),
. ,
, ,
-, -
.
1.1.
-
-
-
, ,
, .
,
-, -, - ( 1.2),
.
,
,
13
[3].
R3 -NHNH
2 CH
2N2
1.2
-
, 1,2-
1,4- -
, ( 1.3).
1.3
, -
,
14
- [12].
1,4- ,
1,2- – [13, 14].
- .
, -
1,4-
[2, 15-20], , [11, 21-26] ,
, 5,6- [27, 28] 1,2-
. -
, NH2- ,
(1,2- ) [29-34].
,
,
, , [13, 35-40]
[41-47]
[48-55].
, 1,4- ,
[56, 57],
1 2
, 3 ( 1.4)
1.4
15
, ,
-
1,3- ,
[3, 7]. , . . -
, , ,
, ( 1.5),
1.3.
1.5
1,4- -
5
( 1.6), , 1,2-
[3, 7].
1.6
1,2-
- , 1
- 7 ( 1.7) [57, 58].
, 8,
, ( 1.4)
.
16
1.7
,
1,2- , -
4
9,
10 - (X = NH) (X = O),
( 1.8).
1.8
.
,
13 ( 1.9) [59, 60]
,
[3].
R1 R
O
N
RR1
O
R2
+ 2 R2-NH2[R2-NH2I]+I-
R2
R311 12 13
R3
R2
1.9
17
-
, , -
- .
-
1- ,
N-
[61]
-
1.3.
1.2.
( I, 1.1),
.
,
, . ,
,
, 1850 [62] ( 1.10):
1.10
,
, 19 ,
, [63-
18
66]. ,
,
. [67],
– - [68-70], [71,
72], [73], [74, 75], ,
[76] [77].
( 1.11). , -
, - ,
- ,
–
- [78].
O
H2N
H+
H2N
OH
HN
OH
O H2N N
O
+ H+ NH
HO. . .
H H
- H+
+ H+- H+ . . .
1.11
18
17 ,
14
15 16,
( 1.12) [63].
,
19
20, ,
, ,
( 1.12) [58].
19
1.12
. 1,4-
, ,
[79-81], ,
[79], [82] [83],
[84-87] [88]
.
18
17 , , ,
, ,
, ,
[3, 7, 89-94].
18, ,
[85]
[91, 92, 95].
,
4-
20
, [84, 96, 97],
23 24 ( 1.13). ,
,
, in situ
.
1.13
,
–
- . , ,
25 - 26 27
28 (
1.14) [98].
.
1.14
,
1,3- 29 30, 31,
–
32 ( 1.15).
21
1.15
[99-112].
–
,
[104, 111], - [105]
[109].
N- 32 (R2 = H).
( 1.15)
33,
, [103, 113].
38 ( 1.16) [63]. ,
34
( ) - 33 36
35 [58].
,
[114-116]
22
1.16
,
39 40
41 ( 1.17) [66, 117].
42 [118-125].
1.17
[118]
42
43 44
( 1.17). , ,
[118]
23
. ,
,
46 [58].
42,
47,
48 [118, 126-128].
, [127] , 48
47, 3-
-5- -2(5 )- 50 ( 1.17).
51
52, 53 ( 1.18)
[129-131]. - (
) 53 ,
,
48.
1.18
[132]
57
( 1.19) [133].
1.19
24
,
[132],
,
,
. ,
.
,
, ,
, (single reactant
replacement – SRR [134]).
,
,
, .
[134-136]
- ,
[65].
-
58, 59 60,
61 ( 1.20).
,
,
[137].
25
1.20
,
[138-140]
,
,
[41, 46, 53, 110, 141-148].
.
30- [149],
, 65,
( 1.21).
1973 . [150] ,
,
67
. ,
,
68.
1997 . [151].
, ,
63, N- 64,
- , 66 ( 1.21).
69
, ,
70.
26
1.21
, -
, .
64
[151],
66 69,
-
71 72, ( . 1.1).
EtO
O
O
NH
NH2
OPh
NH
NH
O
O
EtO
Ph
HO
F3C71 72
. 1.1.
[143]
, N,N'- ,
. [152]
,
N,N'-
27
,
. [153],
76 ( 1.22) ,
,
.
73-75 4-
,
, -
.
1.22
,
[153],
N- ( )
77 ( 1.23).
1.23
28
N,N’- ( )
78.
, , [154-
156].
, ,
,
.
,
.
,
N-
,
, , - ,
, , ,
, ,
[141-145].
, ,
,
, ,
[146]. ,
, ( 400 ),
,
.
.
,
, ,
29
[45, 46, 142, 143, 147,
157-160]. ,
[53, 88, 161-
167], [168]
[169].
,
[71, 72].
20- [73]
,
[170-179].
, ,
, - .
,
,
. , N-
84 [180, 181].
[181]
79, 80, 81
82, ,
83, 84 ( 1.24).
1.24
30
, .
85,
86, 87 88, -
90 ( 1.25) [182].
PhCHO
CO2HPh
O
CN
R NH2
Ph N R
OPh
O NR
PhOPh
I - MeOH, r.t., 24 ;II - KOH, MeOH, r.t.,1-2
+
89 90
85
86
87
88
I II
NHO
NHO
1.25
, , ,
, ,
, ,
[67].
94 ( 1.26) [68].
[69, 70],
, [183],
- .
1.26
31
[184-187]. , 9-
[3.3.1] 96
1,3- 95,
92 ( 1.26).
. ,
- 100 98,
, 97
99 ( 1.27) [67, 188]. , -
- .
, , ,
101
[3.3.1] 102 [189],
103 [190].
1.27
1962 - 106,
,
[191].
1.27,
32
104, 105 .
, ,
, [192].
,
, ( - )
- , -
[193]
.
,
- [110, 194]. , ,
1,3-
107, , -
108, 109,
[195], 112
113 ( 1.28).
1.28
-
110.
,
33
, 111, ,
, , 112
113 [110, 194, 195]. ,
,
-
[196]. ,
115 2
114 , R2,
116, [3.3.1] 117 ( 1.29).
, –
,
.
1.29
,
, 1.3.
,
.
. ,
, , ,
34
,
. , ,
(ABC-
), (ABB- )
(AAA- ).
ABB' , - , ,
, [197].
,
1.3 1.70, 1.86, 1.87.
, [198]
: , ; -
; ,
. .
, ,
[135].
1.3. -
.
-, -, -
-
.
35
1.3.1.
. ,
- ,
–
( II, 1.1)
.
( 1.9) . , [59]
- 119 118
( 1.30).
-
N- .
[60]
121
120, ( 1.30).
1.30
,
, N-
124
[199-202]. , –
36
. , [4.1.0] 125 ( 1.31)
21% [199].
1.31
, 126, S,S-
127 ( 1.31) [203, 204],
.
- . ,
[4.1.0] 125
123 N-
(129) [205]. [206]
, 129
130
,
( 1.32).
1.32
37
,
131 - -
,
- .
,
- : N,N’-
-1,4- [2.2.2]
[207, 208]; N,N- [209]; [210];
[211]
[212]; ,
[213].
, ,
. ,
[214], -
( 1.33).
1.33
- .
N-
[214-220]. N-
, [221,
38
222], [218, 221, 223-226] [226-229].
,
, ( , 133
135, 1.34).
1.34
-
-
[219, 230],
. ,
, - [218, 221, 231-234]. ,
138
- 136 137 ( 1.35) [234].
1.35
39
- - [235], - - [234] - [236]. ,
141 -
139 140
( 1.35) [236].
[3].
, [237-241], -/ -
-
,
. , ,
-
.
.
N- ,
,
- 142,
[207, 221, 242-
244], [245]
( 1.36). , ,
119 99% [244].
1.36
40
[246] – N- 145
- 143 N- 144.
,
-
- .
[247] - 3,5a- -1H-
[1,2-c] 148 -2-
-3- 146
, , (
1.37). :
148 -
.
1.37
[248-251].
, - 149
147,
150 ( 1.37) [252, 253].
,
, ( , 1- -2,3-
41
-3-(4- ) -1- ),
150 [254].
. [247] ,
152,
153,
( 1.38).
, 153.
1.38
[253],
, ,
[255],
. , [253]
,
,
( 1.39).
1.39
42
156 154
155
- (
1.40) [256].
156 R
2 8. -
- .
N N
Ph
R
HR
H
H
R = Ar, C(CH3)3
MWPh
OCl + R O
AcONH4 / AcOH
154 155 156
1.40
, [247, 252]
- -
.
[248], , -2-
-3- 119 157
- - 158 158 , ( 1.41),
.
1.41
,
, [249, 251, 254, 257].
[258]. 1,3,4,6a- [1,2-a] 161
43
1,1 - [1,2- ] 163
159 160 1,2-
162 ( 1.42).
1.42
,
[259]
4- -1,2- 166 ( 1.43).
1.43
168-170,
, -
165, , ,
167,
44
- 168, 169
170.
, .
, , 169
N,N-
.
168
1,5- ,
.
1.3.4.
166 [259]
4- - 4- -1,2- [260].
5- 1,1 -
[1,2- ] 169, 6-
. , ,
, ,
.
1.3.2.
,
-
1,2- 1,3-
. ,
, ,
.
, , , -
.
45
20- [261].
[262] 118
,
1- 171 2- 172 ( 1.44).
[263]
1- 173.
1.44
[264, 265]
1- 2- 171 172,
[263]
.
-
(« » « », 1.45),
A-E F-J.
1.45
46
[11, 266-268]
,
« », ,
– 2-
.
, , 174, 175 [269-
271], 176, 177 [269-273], [274, 275],
[269-271, 276]
178-181 ( 1.46).
1.46
E Z 174-177
- (E- 174-
177), - (E- 174-177) 178-181.
,
- , -1- 178-181
-2-
182-185
24 [269-271].
-
1,2- , ,
47
, 1.1 (
1.8).
[3],
[277-279]
[279] . ,
,
189 ( 1.47). ,
,
.
1.47
, [280] ,
186 2,2- -1-
(DPPH) -78 ° 187,
188
. DHHP ,
, 189.
- –
- . ,
-4- 190 191
192 193,
( 1.48) [281].
48
1.48
-
, - ,
- [3]. , 2- 194
-
195 ( 1.48) [282].
[283]( 1.49).
1.49
, , 196
197 (R = H) -
[2H] 198, 4-
(R = NO2) - 200
( 1.49). ,
199.
49
, ,
- ,
202 [284]. , 201
- 203 ( 1.50).
1.50
. [285]
204 ,
–
-
205,
, ,
- ( 1.50).
1.3.3.
,
,
.
,
, , ,
50
1.2, ,
-
.
, ,
( 1.51):
- , ,
,
(“a” “b”);
-
(“c” “d”);
- ,
(“e” “f”);
- ,
.
1.51
( «b»),
( 1.2),
. ,
51
[286] 206 ,
207,
208 ( 1.52).
[287] ,
209 5-
[1,2-a] 210,
211.
1.52
( ,
213 215),
( 1.53) [288].
1.53
, - ,
52
« » –
in situ [3]. , ,
,
– 1- . ,
[289], 218
219 - 220
(CAN)
221,
- , 222 ( 1.54).
1.54
,
-
-
( “c” “d”, 1.51).
,
.
. , , ,
25 , 6 / 7 -
[290, 291]. ,
,
,
53
,
.
[41, 46, 53, 110, 141-147].
[148].
,
,
, ,
.
[292],
. -D-C- , -
- ,
,
226, (
1.55).
.
1.55
54
,
, [292] ,
, - , -
(227-229). 230, -
, ,
5% - -
.
[292] 4-
- - 4- - - 233
(n = 0 1, ) c 231 (n = 0)
(n = 1). R S (
)
n = 0 5:1, n = 1
( 1.56).
1.56
, ,
, . , ,
[293]
234, 235
95% ee ( 1.57).
(>95% ee) 236
1A (S)-
L771688 ( 237) [294]. ,
55
237 1A
[295].
1.57
[296, 297], –
.
.
– . ,
[298]
.
243
241
ee 80 – 99% ( 1.58). , ,
242 (SQ-32926, ~98% ee)
58%.
56
1.58
244 245 [148]. ,
,
246 ( 1.58). 244 245
ee 88 – 97%
[148].
,
,
- .
, , ,
[299, 300]. ,
, 247
–
250 –
248 249 ( 1.59) [299].
57
1.59
,
,
[300].
-
,
,
.
, . ,
[301] [302, 303]
,
[304, 305]. ,
, ,
[277, 306, 307].
-
3,4- -2- ,
58
251 (X = O, 1.60).
. , ,
3,4- -2- 251 (X = S, 1.60).
1.60
N- ,
.
, 252
253
254 [308], N-(4- ) 255
256 257 [309] ( 1.61).
1.61
258, KOH
259 ( 1.61) [310].
59
260 (n = 1,2),
, 261 (k = 1-3)
262, ,
( 1.62) [311]
1.62
263
- 264, ,
265 ( 1.62) [312].
1,3-
,
,
,
251 (X = NH, 1.60) [313]. ,
,
.
- - [314],
[315], ,
. ,
60
266 216
4- 267,
268 ( 1.63). 267
6- -6- -4- -1,4,5,6-
-2- 269.
1.63
, 5-10 ,
266 216
1,4- -2- 270,
268. ,
271,
.
-
, ,
- , 274-
277 ( 1.64) [316-318].
61
1.64
1,3- . ,
[319-324].
1,4- , 279 [320] 282
[324],
1,3- -4- 284 [323],
,
285 [322] ( 1.65).
1.65
1,3-
, -
.
62
,
[3, 7,
325-327].
-
,
.
,
, 3- -1,2,4- 287 [328], 5- 289 [329], 5-
291 [330, 331], 2- 293 [332], 2-
295 [333] ,
( 288, 290, 292,
294, 296, 1.66).
,
( 1.4, 1.1).
1.66
,
. , [334]
, 2- 297
63
118 298. ,
[335],
- 300,
299
( 1.67).
,
,
[336] . ,
5- -3- 301 -
302 ,
( 1.67) [330, 331, 337, 338].
1.67
[3, 7, 326, 327] –
-
, , N(2) 3- -1,2,4- , N(1) 5-
(3) 2- . ,
, , 305,
[339] ( 1.68). ,
306, 308 309
, N(1), N(2) N(4) .
307.
64
N
N
NH
NH2
Ph Ph
O
O+
N
N
N
NH2
Ph
OPh
O
306
N
N
N Ph
OPh
O
NH2
N
NH
N
N
OPh
Ph
N
NN
Ph
O
Ph
O
NH2 N NH
N N
O
Ph Ph
N
N
N
N
OPh
Ph
Ph Ph
O
O+
307 308
307 +N N
N N
O
Ph Ph
309
287 305
- H2O - H2O
1.68
.
« - »
,
, ,
,
,
.
, 3- -1,2,4- 287
310 311
313,
312,
314
315 316 [340],
.
317 ( 1.69).
65
1.69
[341]
3- -1,2,4- 287
318.
– 319 320 ( 1.70).
[342]
287
( )
320 321 (R = Ph,
R1 = H).
– .
321 [343]
287
.
319
-
. , [340, 341]
, ,
319.
66
1.70
, -
. ,
322 [344-346], 295 [347]
328 [348] 325 326,
323
324, 327
329 ( 1.71). Ar
O
O O
O
+ ArONHN
NR NH2
N
NH
N
N
Ar O
R
322 323 325 326324 R = H, CH3S, NH2
N
NH
N
Ar O
295 + 325 + 236
NHN
NH2
R
327
+ 323 N
NH
NAr O
R
328 + 325 + 326
329 R = CN, COOEt
233 +
N
HN
NH2
295
+ 323
+
328 1.71
330 - ,
, 332,
, 331 (
67
1.72) [349-355].
333.
1.72
3- -1,2,4- 5-
( 1.73), [353].
1.73
,
337 335
334, ,
336. -
.
,
339, ,
338.
,
68
,
.
, 338, [354],
4,4,4-
-1- -1- -3- ,
.
[355] « »
–
- , -
.
,
342,
343 ( 1.74). ,
342 [355]
1 13 , , ,
.
1.74
, ,
[356]. ,
5- -3- -1,2,4- 344
345 346
- 80 °
69
– 347 348 ( 1.75).
348.
NHN
N NH2SH3C
Ar
OO
RO
O
+TSA / H2O N
NH
N
N
Ar
R
O
O
SH3C
+ N
NH
N
N
HO
Ar
O
O
SH3C
R
347 348344 345
346
1.75
.
3- 5- ,
(N) 4-
(CH) . [357, 358] ,
R = CH3 349 325
350,
, [3,4-b]-
351 ( 1.76).
[359].
1.76
3- -5- 349 (R = Ar2)
1,3-
70
. , [358]
, , 3- -5-
, [3,4-b]-
352, [360]
352, -
[5,1-b] 353.
,
.
( 1.77).
1.77
I
in situ ,
- . II III
319,
I.
,
–
( 1.78).
71
1.78
, III ( 1.1 1.77)
4,5-
[361, 362] 6,7- [363]. ,
,
,
.
1,3- ,
, .
6-
[364-377]. ,
- ,
.
, , ,
354,
( 1.79) [364, 366].
[365, 366] 6-
[2,3-d] ,
.
,
( , 358 361, 1.79)
359 363 [373, 374].
72
1.79
. , [378]
5,6- -1,3- 360 1,3- 364
365 ( 1.80).
[4,5-b] 366
60%.
1.80
369
[379].
73
.
369 90%
.
–
, 367 368,
.
[380] 6- -
2-5 ,
87%. , 6-
-1,3-
, 6-
-2-
.
,
, , 1-
- -3- [381]
[382].
1.3.4. 1,2- .
1,2- -
.
,
,
,
,
, - .
74
, 1,2- -
1905 [383],
2,3- -1,5-
50 [384].
1,2-
370 371 [385, 386],
-
372, 1,5-
373,
374 ( 1.81).
373, ,
[3].
1.81
. , 370 - 375
376 [3],
- 213
377 ( 1.81) [387].
, -
75
1,5- [388, 389].
370 378 –
379 ( 1.82). , 380
1,2- 381
[390].
1.82
1,2- -
, , ,
4-
-, 4- -, 4,6- -, N- 1,2-
[3]. 1,4-
, 1,2- [391], (1H-
[d] -2- ) [392], 1,2-
[393-395], [396], [397, 398], [399, 400]
. ,
.
76
, , 1,2- ,
, , 1,2- 383, 3,4-
384 1,2,4- 385 382
386-388 ( 1.83) [333,
401, 402].
1.83
382 1,2- -4-
389 -
3,4- [1,5-b] -7- 390,
391 [403].
1,5- ,
– 392 392 ( 1.84).
[404, 405],
392 , 394,
393.
77
1.84
1,2-
5,6- -1,3- 395 396 ( 1.85).
[27, 28] ,
,
[406] 397
398.
399.
1.85
1,2-
( 1.86).
1951
1,2- [407],
78
,
.
1.86
, , [408], [409],
[410], [411].
,
[412], MoO2Cl2 [413], [414], [415],
[416] . .
1,5- ,
, ,
1,2- , , ,
[417],
- .
. , 1,2-
401 402
403 404 ( 1.87) [259, 411,
418].
R, R1 R2 - R
79
,
.
R1 R2
,
.
1.87
, , , 405,
, 407 [419].
1,2-
[417, 420-422].
(I – III, 1.88), ,
, .
1.88
80
I II
; III
in situ - . II
III, - ,
I .
* * *
, (
[423-427]) ,
,
[134-136]
.
,
, ,
,
,
, ,
,
.
81
2
2
,
,
,
.
,
[121, 122, 428-434],
.
,
( I, IV
II, III, . 2.1), ( I, II III, IV)
,
.
X
NH
NH2 RY
O
Ar
O+
X = N, CH;R = H Ar1, Y = COOR1; R = CH3CO, Y = NHR1 OR1R = H Ar1, Z = OR1; R = CH3, Z = NHR1 OR1
X
NH
N
Ar O
Z
R
N
NH
X
Ar O
Z
R
X
NH
N
R O
Z
Ar
N
NH
X
R O
Z
Ar
I
II III
IV
. 2.1.
2 ,
1
82
(R = H, Ar1, Y = COOH, . 2.1) (R =
CH3CO, Y = NR1) . , ,
,
, , ,
.
2.1.
2.1.1.
- CH- 1,3-
, , ,
, ( . 1.1).
1
2 - 5- 4 5- -1,2,4- 5 ,
II ( 2.1)
3 - .
,
3 - 5- 4
7-
-4,7- [1,5-a] -5- 6 -
( A, 67-80%, . 2.1), 3- -1,2,4-
4 ,
7 - 8 - ,
( B),
[435].
83
2.1
7 -
,
8 - ,
, , ,
( . 5).
, [ . 1.3.3
423, 426], 3- -1,2,4-
( 7 - ).
, , ( 1.68) [339].
,
7 - 8 - ,
1 2 - 3- -1,2,4-
84
5 , ( I, , 2.1).
42-65%
-5- 7 - ( D) [436].
5- , « » ,
1, 2 - 4 ,
6 - , , ( F, 55-65%, . 2.1).
2.1 6-9, 11
( )
R R1 , (%)
3 (2 ) C6H5 4 - 6 57 55 3 (2 ) 4-CH3OC6H4 4 - 6 69 60 3 (2 ) 4-ClC6H4 4 - 6 80 62 3 (2 ) 4-FC6H4 4 - 6 75 54 3 (2 ) 4-BrC6H4 4 - 6 68 65 2 (2 ) 4-CH3OOCC6H4 4 - 6 - 59 3 (2 ) 2,5- CH3OC6H3 4 - 6 - 46 3 (2 ) C6H5 5 H 7 60 51 3 (2 ) 4-CH3OC6H4 5 H 7 76 56 3 (2 ) 4-ClC6H4 5 H 7 82 47 3 (2 ) 4-FC6H4 5 H 7 62 58 3 (2 ) 4-BrC6H4 5 H 7 60 65 3 (2 ) 4-CH3OC6H4 5 CH3S 7 78 52 3 (2 ) 4-ClC6H4 5 CH3S 7 62 56 2 (2 ) 4-CH3OOCC6H4 5 H 7 - 52 3 (2 ) 2,5- CH3OC6H3 5 H 7 - 42 3 (2 ) C6H5 5 H 8 * 14 20 3 (2 ) 4-CH3OC6H4 5 H 8 * 12 19 3 (2 ) 4-ClC6H4 5 H 8 * 9 16 3 (2 ) 4-FC6H4 5 H 8 * 15 23 3 (2 ) 4-BrC6H4 5 H 8 * 19 31 3 (2 ) 4-ClC6H4 5 CH3S 8 * 32 - 2 4-CH3OC6H4 5 H 9 - 43 2 4-ClC6H4 5 H 9 - 68 3 (2 ) 4-CH3OC6H4 10 - 11 56 48 3 (2 ) 4-ClC6H4 10 - 11 61 51 3 (2 ) 4-BrC6H4 10 - 11 52 50
* ; – , ( II, 2.1); – , ( I, 2.1)
85
( , , 2- ), ( -
)
, ,
, .
,
3- -1,2,4- ,
,
,
.
, , .
,
120 °
.
. , ,
1, 3-
-1,2,4- 5 , 2 ,
(25 ° )
7- -4,5,6,7-
[1,2,4] [1,5-a] -7- 9 ,
( E, 2.1).
5- 4
–
( G, 2.1). ,
, 5-
3- -1,2,4- . ,
86
5- -
[437]
[438]
( 200 ° ), , ,
.
3 -
4, 5 , –
.
9 ,
~50 ° ,
( , 3- -1,2,4- ),
7. ,
, ,
9 , ,
7, .
2.1.2
( 2.5 2.6).
. ,
,
1 2 , , 3,5- -1-(4-
)-1,2,4- 10 ( 2.2, I II, )
12 3-{[5- -1-(4- )-1H-1,2,4- -
3- ] }-5- -2(5H)- 11 - [439] ( . 2.1). ,
10
87
, , ,
-
.
N
N
N
NH2
Cl
H2NOH
O
OR
3 , ,
N
NH
N
N
Cl
HN
R
O
OH
N
N
N
NH
Cl
H2N
11 -(48-61%)
O
R
O
,-H2O
OH
O
OR O+
-2H2O
1 2 , ,
-H2O
NaOH, EtOH/H2O 10
10, HOAc, 12I
II
2.2
5- , - NH2-
CH NH ,
,
[440-444].
,
1- 3- 5-
, ,
[445, 446]. 3- -5-
13
3 ,
88
4- -3- [3,4-b] -6- 14 ,
( 2.3, II . 2.2).
2.3
,
, 1.
5- -3- -1-
3 3 , ,
-6-
14 , .
15 ,
. ,
ó
( ., , 3.3.2, 3.12).
3 - 3- -5-
13 ,
89
.
2.2 14-17
( )
R R1 R2 , (%)
3a C6H5 13 H CH3 14a 38 3 4-CH3OC6H4 13 H CH3 14 42 3a C6H5 13 C6H5 CH3 14 39 3 4-CH3OC6H4 13 C6H5 CH3 14 48 3a C6H5 13 C6H5 CH3 15 68 3 4-CH3OC6H4 13 C6H5 CH3 15 72 3a C6H5 13 H C6H5 16a 75 , 78
3 4-ClC6H4 13 H C6H5 16 78 , 80 14 31
3 4-CH3OC6H4 13 H C6H5 16 15 +14 *
52 , 76 26 ,
3a C6H5 13 H 4-BrC6H4 16 65 , 68 3 4-ClC6H4 13 H 4-BrC6H4 16 76 , 76
3 4-CH3OC6H4 13 H 4-BrC6H4 16 14
48 , 83 22
3 4-CH3OC6H4 13 H 4-BrC6H4 15 56 2 C6H5 13 H CH3 17 42 2 4-ClC6H4 13 H CH3 17 39 2 4-CH3OC6H4 13 H CH3 17 42 2 4-CH3C6H4 13 H CH3 17 32 2 C6H5 13 C6H5 CH3 17 38 2 4-ClC6H4 13 C6H5 CH3 17 44 2 4-CH3OC6H4 13 C6H5 CH3 17 42 2 4-CH3C6H4 13 C6H5 CH3 17 36 2 C6H5 13 H C6H5 17 42 2 4-ClC6H4 13 H C6H5 17 44 2 4-CH3OC6H4 13 H C6H5 17 42 2 4-CH3C6H4 13 H C6H5 17 39 2 C6H5 13 H 4-BrC6H4 17 40 2 4-ClC6H4 13 H 4-BrC6H4 17 45 2 4-CH3OC6H4 13 H 4-BrC6H4 17 42 2 4-CH3C6H4 13 H 4-BrC6H4 17 46 2 2-CH3O-5-BrC6H3 13 H 4-C2H5C6H4 17 44 2 4-FC6H4 13 H 4-BrC6H4 17 46
– HOAc – – HOAc 25 ° – HOAc – 15
* – 14
, 3 13 ,
3 13
16 , , . ,
3 5- 13
90
14 ,
16 .
13 ,
3 , .
, 13 3 2-
-7-(4- )-4,7- [1,5- ] -5- -
16 ( ) – 3- -4-
(4- )-4,7- [3,4-b] -6-
15 14 ,
( 2.3, . 2.2).
13 3
16 ( ) 14 ;
15
.
.
.
, 3- -5-
. ,
3 ,
13 , 25 °
68 – 80%
16 - ( 2.3, . 2.2).
5- 13 -
1 2 - , ,
, ,
, 6-
[3,4-b] -4- 17a-
91
50% ( 2.3, I . 2.2).
.
,
,
.
1 2 - , ,
5- -N- -1H- -4- 18 - [447],
,
.
, –
3 - , , 18 -
–
19 - 20 -
( 2.4), 11 ( 2.2).
,
,
.
2.4
92
, ,
20 , , , .
(68-83%)
,
, 19.
19 - , , ,
, 21 - ,
.
2.3 19, 20
( )
R R1 , (%) A
3 (2 ) 4-CH3OC6H4 18a C6H5 19a 68 , 72 46 3a (2 ) C6H5 18 4-C2H5OC6H4 19 68 , 70 52 3 (2 ) 4-ClC6H4 18 4-C2H5OC6H4 19 72 , 78 58 3 (2 ) 4-CH3OC6H4 18 4-C2H5OC6H4 19 68 , 68 40 3 (2 ) 4-CH3C6H4 18 4-C2H5OC6H4 19 65 , 70 51 3 (2 ) 4-ClC6H4 18 4-CH3C6H4 19 58 , 74 49 3 2-ClC6H4 18 4-FC6H4 19 48 , 69 --- 3 4-CH3C6H4 18 2-CH3 C6H4 19 76 --- 3 4-ClC6H4 18 4-C2H5OC6H4 20 25 , 75 --- 3 4-ClC6H4 18 4-CH3C6H4 20 29 , 83 --- 3 2-ClC6H4 18 4-FC6H4 20 30 --- 3 4-CH3C6H4 18 4-FC6H4 20 70 --- 3 4-ClC6H4 18 4-FC6H4 20 68 --- – HOAc (120 ° ) – MeOH – HOAc (170 ° )
A – , ( II, 2.4) – , ( I, 2.4)
, ,
, ,
[447]. ,
93
3 - , ,
18 -
19. 170 °
19 -
68-74% ( 2.4, . 2.3).
-
19 -
1, 2 - , 18 ,
( 2.4, I).
, , 3-
5- ( 2.3), 5- -N- -1H-
-4-
– 7-
-3-( )-4,7- [1,5-a] -5- -
19.
3- -1,2,4- 5-
( 2.1).
2.1.2.
,
,
.
1,3-
.
,
.
94
, 22 -
2 - , 5- 4, 3- -1,2,4-
5 , 3- -5-( )-2H-1,2,4- 5 3,5-
-1-(4- )-1,2,4- 10
,
, [448].
,
. , , 2-3
5 , , 2 - , 22 -
7- -5,6- -4,5,6,7- -
[1,2,4] [1,5-a] -7- 23 - ( ,
2.5, . 2.4), 9 , ( ,
2.1) [449].
2.5
180
7,
24 - ( , 2.5, . 2.4). ,
95
,
( , D, 2.1 , 2.5).
2.4 23-26
X R3 R1 R2 ,(%)
5 H 22 H 2 H 23 79 , 62 5 H 22a H 2 Cl 23 76 , 69 5 H 22a H 2 CH3 23 68 , 56 5 H 22 CH3 2 H 23 68 5 H 22 F 2 H 23 68 5 H 22 H 2 CH3 23 65 5 CSCH3 H 22 H 2 H 23 63 5 CSCH3 H 22 H 2 Cl 23 71 5 CSCH3 H 22 H 2 CH3 23 76 5 H 22 H 2 H 24 56 , 59 5 H 22a H 2 Cl 24 72 , 70 5 H 22a H 2 CH3 24 60 , 63 5 H 22 CH3 2 H 24 62 5 H 22 F 2 H 24 66 5 H 22 H 2 CH3 24 68 5 CSCH3 H 22 H 2 H 24 70 5 CSCH3 H 22 H 2 Cl 24 75 5 CSCH3 H 22 H 2 CH3 24 72 4 N H 22 H 2 H 24 60 4 N H 22a H 2 Cl 24 67 4 N H 22a H 2 CH3 24 52 4 N H 22 CH3 2 H 24 56 4 N H 22 F 2 H 24 59 10 CNH2 4-ClC6H4 22 H 2 H 24 59 10 CNH2 4-ClC6H4 22 H 2 Cl 24 78 10 CNH2 4-ClC6H4 22 H 2 CH3 24 63 18 --- --- 22 H 2 H 25 72 , 68 18 --- --- 22 H 2 CH3 25 83 , 80 18 --- --- 51 H 2 Cl 25 85 18 --- --- 51 H 2 CH3 25 78 18 --- --- 51 H 2 H 26 75 ,72 18 --- --- 51 H 2 CH3 26 79 , 77 18 --- --- 51 H 2 Cl 26 82 , 18 --- --- 51 H 2 CH3 26 77 , – , ( I, 2.5 2.6) – , ( IV, 2.5 2.6)
96
, ,
. ,
30
[1,5-a] -7- 23 -
( , 2.5).
,
.
23
, 24 – .
24
(170 ° , 20 )
180 ( , 2.5).
, 23 -
-
-d6 ( ) ~50 °
–
, 3- -1,2,4-
( 2.5). 23 -
(170 ° , 40 )
24 - .
,
5- 4 3,5-
-1-(4- )-1,2,4- 10
23 -
.
4, 10, 22 -
97
2 , , 24 - ( ,
2.5, . 2.4).
-
,
25 - (
IV, 2.5). ,
–
23 - ,
24 - ( C D,
).
5- -N-(4- )-1H- -
4- 18 , 22
2 - ,
.
HO
Ac,
MW
,170
o C,
20 - H2O
2.6
,
25 °
98
3-(4- )-7- -5-
-6- -4,5,6,7- [1,5-a] -7-
25 - ,
170 ° ,
N-(4- )-5-(5- -3-
-2- -4- -2,5- -1H- -1- )-1H- -4-
26 - ( 2.6, . 2.4).
, 25 - ,
9 , 23 - , 50-60 ° ,
,
26 - .
,
27 , ,
25 , , (MW, 170 ° , 20 )
( 26 , , 2.6, . 2.4).
,
,
, ,
.
( . 2.2, 3.1 3.2).
,
3- 5- 13 ( 2.7). , 3- -
3- -1- -5- 13 , c
22 2 , ,
28,
99
( 2.3),
4,5- [3,4-b] -6- 29 - ( 2.7,
. 2.5).
2.7
2.5 29, 30
R1 R2 , (%)
13 H 22 2 OCH3 29 32 13 H 22 2 Cl 29 38 13 H 22 2 CH3 29 28 13 C6H5 22 2 OCH3 29 36 13 C6H5 22 2 Cl 29 40 13 C6H5 22 2 CH3 29 42 13 H 22 2a H 30 52 13 H 22 2 Cl 30 65 13 H 22 2 CH3 30 57 13 H 22 2 CH3O 30 53 13 Br 22 2a H 30 37 13 Br 22 2 Cl 30 56 13 Br 22 2 CH3 30 41 13 Br 22 2 CH3O 30 34 13 CH3O 22 2 H 30 56 13 CH3O 22 2 Cl 30 67 13 CH3O 22 2 CH3 30 50 13 CH3O 22 2 CH3O 30 52
5-
–
100
3- -5- 13 , ,
22 2 - , 5-(4- )-3- -
4- -1-(3- -1H- -5- )-1H- -2(5H)- 30 - ( 2.7,
. 2.5), ,
18 ( 2.6).
,
9 , , 23 - 25 -
–
, -
, 50 °
.
6, 7, 14, 15, 16,
17, 19, 29 . ,
,
.
, ,
, ,
- [423]. ,
6 , 7 ,
31 - ( 2.8).
2.8
HBr 32 -
.
101
.
2.2.
( . 1.3.3, 1.72 ).
,
,
.
, ,
, ,
[450],
- . 1,3-
5- -1,2,4- -3- 3- 5-
.
5- -1,2,4- -3- 33
,
, S-
[451]. 38
, ,
( 2.9), S-
35 36 - .
5- -1,2,4- -3-
33, 2 - , , -
34 - : ,
102
120 200 ° ,
(HOAc, HCl) ó (Et3N, N-
) .
-
5- -1,2,4- -3- 33,
.
2.9
( 2.9),
S- .
3- -5- -1,2,4- 37 -
2 - , , -
34 - . ,
: ,
, , - , ,
.
( . 2.6), ,
,
,
.
(120 ° , 5 ).
103
2.6 2 - , , - , 34 - 37 -
, , %
3 78 20
3 101 0
- 1 118 30
- 1 97 60
15 153 50-70
5 120 70-90
- 5 120-150 40-60
2 120-150 60-90
38 -
( . 2.7), , ,
250 .
,
ó ,
. ,
2.1.1 2.1.2 ,
.
, 3- -
5- -1,2,4- 37 , 22 , , ,
34 , ,
4,5,6,7-
[1,2,4] [1,5-a] -6- 39 - (
2.9, . 2.7).
9 , , 23 - 25 - 39 -
50 – 60 °
-d6 ;
38 -
180 .
104
2.7 38, 39
R2 R1 R ,(%)
37 H 34 C6H5 2 C6H5 38 45 70 37 H 34 C6H5 2 4-FC6H4 38 65 87 37 H 34 C6H5 2 4-ClC6H4 38 78 90 37 H 34 C6H5 2 4-BrC6H4 38 80 95 37 H 34 4-ClC6H4 2 4-FC6H4 38 65 85 37 H 34 4-ClC6H4 2 4-CH3OC6H4 38 58 85 37 H 34 4-ClC6H4 2 2-FC6H4 38 55 85 37 3-CH3C6H4 34 C6H5 2 C6H5 38 47 78 37 3-CH3C6H4 34 C6H5 2 4-CH3OC6H4 38 58 75 37 3-CH3C6H4 34 2,4-(CH3)2C6H3 2 4-FC6H4 38 55 75 37 3-CH3C6H4 34 2,4-(CH3)2C6H3 2 4-ClC6H4 38 67 90 37 3-CH3C6H4 34 2,4-(CH3)2C6H3 2 4-BrC6H4 38 70 90 37 3-CH3C6H4 34 2,4-(CH3)2C6H3 2 4-CH3C6H4 38 55 75 37 3-CH3C6H4 34 2,4-(CH3)2C6H3 2 4-CH3OC6H4 38 52 78 37 3-ClC6H4 34 2,4-(CH3)2C6H3 2 - 4 3S 38 50 75 37 CH3 34 2-CH3OC6H4 2 2-CH3CH2OC6H4 38 62 76 37 CH3 34 2-CH3OC6H4 2 4-CH3C6H4 38 50 75 37 CH3 34 C6H5 2 4-ClC6H4 38 50 80 37 CH3 34 C6H5 2 4-CH3CH2C6H4 38 75 90 37 C6H5 34 2-CH3OC6H4 2 4-CH3CH2C6H4 38 55 85 37 C6H5 34 4-CH3OC6H4 2 4-CH3CH2C6H4 38 70 90 37 C6H5 34 C6H5 2 4-CH3C6H4 38 65 85 37 C6H5 34 2-CH3OC6H4 2 4-BrC6H4 38 75 85 37 CH3 34 C6H5 2 4-ClC6H4 39 55 - 37 CH3 34 C6H5 2 4- H3 H2C6H4 39 85 - 37 C6H5 34 2- H3OC6H4 2 4-BrC6H4 39 70 - 37 C6H5 34 2- H3OC6H4 2 4- H3 H2C6H4 39 85 - 37 C6H5 34 4- H3OC6H4 2 4- H3 H2C6H4 39 65 - 37 C6H5 34 C6H5 2 4- H3C6H4 39 55 - – ( . 38) ( . 39) –
, 37 - ,
2 - , , - 34 -
, ,
,
, ,
- -6- 38 - 39 - , .
105
18 , 40 , ( 2.10) -
34 , -
2 , , , , - ,
41 - ( ),
42 - ( ).
2.10
,
43 - ,
( IV, 2.10).
. ,
3- 5-
,
( . 2.7).
2 , , - , 34 -
5- 13 , , :
106
,
46 ( 2.11).
2.11
,
.
, 3- -5- 13 34 ,
22 , , , , -
, -, -
, 4,7- [1,5-a] -6-
44 - ( 2.11, . 2.8).
2 , , , ,
4,7- [3,4-b] -5-
45 - .
13 , ,
,
,
-6-
44 - . ,
3- -5- , 3-
( . 2.1.2 3.1.1, 2.3 3.1).
107
2.8 41, 42, 44, 45
R2 R1 R , (%)
18 CONH2 34 C6H5 2 3-CH3O-4- OC6H4 41 70 18 CONH2 34 2,4- CH3C6H3 2 3,4- CH3OC6H3 41 75 40 CN 34 2-CH3OC6H4 2 4-BrC6H4 41 65 40 CN 34 2-CH3OC6H4 2 C6H5 41 80 18 CONH2 34 C6H5 2 4-CH3C6H4 42 85 18 CONH2 34 C6H5 2 4-ClC6H4 42 75 18 CONH2 34 C6H5 2 3-CH3O-4-HOC6H4 42 55 18 CONH2 34 2-CH3OC6H4 2 3,4- CH3OC6H3 42 55 18 CONH2 34 2-CH3OC6H4 2 4-CNC6H4 42 50 18 CONH2 34 2-CH3OC6H4 2 4-ClC6H4 42 75 18 CONH2 34 4-CH3OC6H4 2 3- C2H5O-4-HOC6H4 42 55 18 CONH2 34 4-C2H5OOCC6H4 2 3-CH3O-4-HOC6H4 42 55 18 CONH2 34 2,4- CH3C6H3 2 3,4- CH3OC6H3 42 75 40 COOCH3 34 2-CH3OC6H4 2 4-ClC6H4 42 78 40 CN 34 C6H5 2 4-ClC6H4 42 80 40 CN 34 2-CH3OC6H4 2 C6H5 42 80 40 CN 34 2-CH3OC6H4 2 4-BrC6H4 42 75 13 CH3 34 C6H5 2 4-CNC6H4 44 55 13 CH3 34 C6H5 2 4-BrC6H4 44 50 13 CH3 34 C6H5 2 4-NO2C6H4 44 65 13 CH3 34 C6H5 2 4-HOOCC6H4 44 50 13 CH3 34 4-ClC6H4 2 4-NO2C6H4 44 50 13 CH3 34 C6H5 2 C2H5O-4-HO-3-C6H3 45 55 13 CH3 34 C6H5 2 3,4- HOC6H3 45 35 13 CH3 34 C6H5 2 3,4- CH3OC6H3 45 45 13 CH3 34 C6H5 2 4-HOC6H4 45 42 13 CH3 34 C6H5 2 4- (CH3)2NC6H4 45 50 13 C6H5 34 C6H5 2 3-CH3O-4-HOC6H3 44 55 13 4-CH3OC6H4 34 C6H5 2 4-ClC6H4 44 52 13 4-CH3OC6H4 34 C6H5 2 3-CH3O-4-HOC6H3 44 55 13 4-CH3OC6H4 34 C6H5 2 4-BrC6H4 44 65 13 4-CH3OC6H4 34 2-CH3OC6H4 2 4-BrC6H4 44 50 13 4-CH3OC6H4 34 2,4- CH3C6H3 2 4-BrC6H4 44 65 13 4-ClC6H4 34 C6H5 2 4-HOOCC6H4 44 65 13 4-ClC6H4 34 C6H5 2 4-CNC6H4 44 52 13 4-ClC6H4 34 C6H5 2 4-NO2C6H4 44 65 13 4-ClC6H4 34 2,4- CH3C6H3 2 3-CH3O-4-HOC6H3 44 65 13 4-ClC6H4 34 2-CH3OC6H4 2 4-BrC6H4 44 55
108
2.3.
,
.
, , –
[3, 7], ,
4, 5, 13, 18
-
( I),
( 2.12).
2.12
,
. ,
3- -1,2,4- 5 N2 N4
, , 7 8, .
5-
N1 C4, ,
, . ,
3- -5- (13 )
,
14, -
109
.
( 13 - ) 4 -
N1 ,
16. ,
( I, 2.3)
5-
, .
3,5- -1-(4- )-1,2,4- 10
[452],
, 11 ( . 2.2). ,
, , R1 H
« » ( 2.12) ,
,
; , « » .
II,
[127]
[27].
- 1,3-
( 2.13).
3 ( « »),
(X = N) (X = CH) (
110
III, « »), IV ( « »),
V ( « ») .
2.13
, , « »,
( . B, C D 2.1). ,
3
[453, 454].
, 6, 7,
8 19
( « »),
- ( « 1»).
,
11, 10,
111
, IV
( « 2»),
( 2.12).
( 17, 9, 23 25),
3- 5-
13
5 18 ( . 2.1, 2.5 2.6),
V ( « »),
.
« 2»
25 - 27 ,
22 - . ,
,
23 25 ( 2.5, 2.6).
5- 13 - (
« 1»).
24, 26 30.
4, 10, 13 18 22
2
VII, ,
[455],
.
VIII -
24, 26 30.
« », VI.
, 2.2.
112
* * *
,
, -
.
, ,
,
, 5- -
[1,5-a] ( ), 7- [1,5-a]-
( ).
. ,
3- -1,2,4-
3- -2- .
-
, 1- -2- .
. 2.2.
113
( . 2.2).
114
3
-
,
,
- 1,3-
.
.
,
, , 1,3-
,
,
. , ,
-, , ,
.
3- 5-
.
(N1, C4 NH2),
,
- ,
( . 1.3.3, 1.76).
115
3.1. 1,3-
5-
3.1.1. [3,4-b] -5-
[5,1-b] -8-
3- -5-
13 , 1,3- 47a,
2 - , , , , ,
[357, 358, 360],
( . . ~80 °C)
, ,
48 49, .
,
, , .
,
,
.
,
.
,
48. ,
( , N-
). , (HCl HOAc)
.
116
R
O
NNH
R2
NH2
O
O
NH
NNH
RR2O
R1
R1
+
13 , , 47 ,
2 - , , , ,
EtOH, NEt3MW, 150 oC, 15
H
49 -(51-70%)
N
NH
NR O
R1
R1R2
EtOH,25 oC, 30
R1
R1
48 -(70-91%)
- 2H2O
- 2H2O
R2 = CH3
R2 = Ar
- 2H2O
CH3CN, (CH3)3SiClMW, 170 oC, 30
R2 = Ar
3.1
3.1 48, 49
1,3-
R1 R2 R , (%)
47 CH3 13 C6H5 2 4- CH3C6H4 48 86 47 CH3 13 C6H5 2 4- CH3OC6H4 48 76 47 H 13 C6H5 2 4-FC6H4 48 85 47 CH3 13 C6H5 2 4-BrC6H4 48 91 47 CH3 13 C6H5 2 4-NO2C6H4 48 83 47 CH3 13 C6H5 2 2-CF3C6H4 48 86 47 CH3 13 C6H5 2 C6H5 48 85 47 H 13 C6H5 2 4-CH3C6H4 48 70 47 CH3 13 4-CH3C6H4 2 4-ClC6H4 48 80 47 CH3 13 4-CH3C6H4 2 4-BrC6H4 48 82 47 CH3 13 CH3 2 4- CH3C6H4 48 74 47 CH3 13 CH3 2 4- CH3OC6H4 48 70 47 CH3 13 CH3 2 C6H5 48 77 47 CH3 13 C6H5 2 4-CH3C6H4 49 56 47 CH3 13 C6H5 2 4- CH3OC6H4 49 61 47 CH3 13 C6H5 2 2-MeOC6H4 49 60 47 CH3 13 C6H5 2 4-BrC6H4 49 70 47 CH3 13 C6H5 2 4-NO2C6H4 49 54 47 H 13 C6H5 2 4-BrC6H4 49 51 47 CH3 13 C6H5 2 C6H5 49 67 47 H 13 C6H5 2 4-NO2C6H4 49 54
4- -3- -1,4,6,7,8,9-
-5H- [3,4-b] -5- 48 - ,
2 - , , , ,
117
13 , , 47 , 1.2
150 °C 15 (
3.1, . 3.1) [456].
,
.
, (5-10 )
,
48
, 2- 4-
.
120 - 140 °C.
48
.
150 °C.
,
,
.
( . 3.1 ) [457,
458].
13 , 47a 2 . 3.1
, 150 °
4-5 .
, ,
150 °C, ,
48 ( ).
. 3
)
3.1.
,
1,
-8(4H
13 , 47a
,
4
.
,
,
,3-
H)- 4
2
48
49
47a,
9-
49 - (
118
[4
,
,
.
,
-2-
3.1).
,
(
( )
44, 459, 46
5-
-5,6,7,9-
)
)
60].
,
-3-
30
,
,
2 , ,
48.
( )
,
,
13 ,
, , , ,
[5,1-b]-
,
,
-
,
119
,
49 .
, ,
48.
ó ,
.
,
5- -3-
13 , 1 2 , ,
49
48 - . ,
,
.
,
3- 5- , ,
49
.
,
,
, , ,
[153, 461, 462].
49,
13,
- 1, 2
170 ° 40 ( 3.1).
120
3- -5- –
48.
,
1,3- , 3- 5-
,
,
[3,4-b] -5- , [5,1-b] -8-
.
3.1.2. 5-
48,
,
1,3- .
3.2
, 5- 13 ,
47a, 2a, , , ,
(EtOH, 150 °C, 15 )
,
- 1H 13C,
( . 5.2)
121
4,5,5a,6,7,8- [4,3-c] -9- 50 - ( 3.2,
. 3.2) [463, 456].
3.2 50
1,3-
R1 R2 R , (%)
47 CH3 13 C6H5 2 4-CH3C6H5 50a 75 47 CH3 13 C6H5 2 4- CH3OC6H5 50 65 47 CH3 13 C6H5 2 4-FC6H5 50 38 47 CH3 13 C6H5 2 4-BrC6H5 50 70 47 CH3 13 C6H5 2 C6H5 50 60 47 H 13 C6H5 2 C6H5 50 58 47 H 13 C6H5 2 4- CH3C6H5 50 60 47 H 13 C6H5 2 4- CH3OC6H5 50 58 47 H 13 C6H5 2 4-BrC6H5 50 59 47 CH3 13 CH3 2 4-BrC6H5 50 54 47 H 13 CH3 2 C6H5 50 60
,
.
( . 3.2 ),
(Staphylococcus aureus), (Candida albicans)
Escherichia coli [464, 465], ( .
3.2 ), .
.
. 3.2.
122
,
,
,
, «
»
.
,
50
48,
150 °
50. ,
1,3-
48.
50
32–45%,
75%
1,3- . ,
,
51,
1 ,
51 .
51 [466]
48 (MW, /EtONa,
150 ° , 15 ) 5- -3- 13 ( 3.3).
123
3.3
( 3.3),
- 47 , c
2 , , , , (EtOH/EtONa (2 ), MW, 100 °C, 10 )
in situ 51 - 5-
13 , ,
( ).
( ),
50 - ,
3- -5- ,
13 , 47 , (EtOH/EtONa, MW,
150 °C, 10 )
2 , , , , .
52.
( ,
),
50 ,
- - ,
124
, 48, 52 9-
53, 51.
( . 3.3). ,
48, 50 .
3.3
(MW, 150 °C, 15 )
/ -
, %
50 48 Et3N/EtOH 0 100
K(Na)OH/EtOH 0-20 80-100
MeONa(K)/MeOH ~40 ~60
EtONa/EtOH 80-100 0-20
t-BuOK/t-BuOH 95-100 0-5
( )
,
.
, , - –
95%,
~75%.
.
, ,
~80 °C
48.
,
,
150 °
.
,
/
(
(
(
.
,
[467, 46
,
150
(150 °C),
( .
48 50
8] ( . 3
,
1
5
0 ° ),
125
13
,
3.1),
0
,
.3).
).
,
.
.
EtON
2
~ 1:1 (
,
3.3.
13
Na/EtOH)
150 °C
48.
3 , 47a
.
.
47a
C
80%).
2
(
.
.
.
126
, ,
, .
3.1.3. 5- -N- -4-
5- -N- -1 - -4- ,
,
( . 2.1 2.2, 2.4, 2.6 2.10).
-
.
, 5- -N- -1 -
-4- 18 , , 2 - , ,
1,3- 47 , 15
, , -3-
54 - ( I, 3.4, . 3.4).
3.4
127
3.4 54, 55, 57
1,3- R1 R2 R , (%)
47 Me 18 C6H5 2 4-CH3C6H4 54a 79 47 Me 18 C6H5 2 4-CH3OC6H4 54 85 47 Me 18 C6H5 2 4-ClC6H4 54 71 47 Me 18 C6H5 2 4-HOOCC6H4 54 71 47 Me 18 4-CH3C6H4 2 C6H5 54 86 47 Me 18 4-CH3C6H4 2 4-CH3C6H4 54 87 47 Me 18 4-CH3C6H4 2 4-MeOC6H4 54 78 47 Me 18 4-CH3C6H4 2 4-ClC6H4 54 92 47 Me 18 4-CH3C6H4 2 4-HOOCC6H4 54 65 47 Me 18 4-ClC6H4 2 C6 5 54 89 47 Me 18 4-ClC6H4 2 4-CH3C6H4 54 90 47 Me 18 4-ClC6H4 2 4CH3OC6H4 54 59 47 Me 18 4-ClC6H4 2 4-ClC6H4 54 64 47 Me 18 4-ClC6H4 2 4-HOOCC6H4 54 78 47 H 18 C6H5 2 C6H5 54 69 47 H 18 C6H5 2 4-CH3C6H4 54 79 47 H 18 C6H5 2 4-ClC6H4 54 89 47 H 18 4-CH3C6H4 2 C6H5 54 79 47 H 18 4-CH3C6H4 2 4-CH3C6H4 54 91 47 H 18 4-CH3C6H4 2 4-ClC6H4 54 90 47 H 18 4-ClC6H4 2 C6H5 54 70 47 H 18 4-ClC6H4 2 4-CH3C6H4 54 75 47 H 18 4-ClC6H4 2 4-ClC6H4 54 63 47 Me 18 4-CH3C6H4 2 C6H5 55 68 47 Me 18 C6H5 2 4-CH3C6H4 55 71 47 Me 18 C6H5 2 4-ClC6H4 55 63 47 Me 18 4-CH3C6H4 2 4-ClC6H4 55 65 47 Me 18 4-CH3C6H4 2 4-FC6H4 55 78 47 Me 18 4-CH3C6H4 2 4-CH3C6H4 55 75 47 Me 18 4-CH3C6H4 2 4-ClC6H4 57 35 47 Me 18 4-CH3C6H4 2 4-CH3OC6H4 57 30
,
,
.
,
18 - , 47 2 - ,
128
-3-
55 - (63-78%),
, COSY, ( .
5.2).
,
, 1 ,
53
54, 55
.
,
56 , ,
–
55 54, .
,
, , ,
,
55 – 25 – 150 °
54. ,
55.
, 5- -N- -1 -
-4- 18 , 2 , ,
1 , ,
, EtOH/H2O (2:3).
-
129
,
54 , 3,3,6,6-
-N,9- -1,8- o o-2,3,4,5,6,7,8,9- -10(1 )-
-1 - -4- 57 , ( 3.5).
35% ( . 3.4),
54 50%.
-10- -4- 57
,
.
57
– ( ,
,
, ,
ó )
54,
, 53.
3.5
,
[99-111], 58
18 , (NEt3),
(HCl) ,
53 (
( ,
3.1.5.
1
. 3.4
),
).
.
.
4.
57
,
.
,
20 °
,
130
7.
-3-
1
,
150
1
-
N-
,
,
0 °
54
N-
,
(
57
4 ,
,
,
. 3.4).
57 , ,
,
131
57 2- ,
CN- ,
( . 3.5).
,
( 19,
20, 25, 26, 41, 42, 54, 55)
,
.
,
,
Ar R1
( . 3.6).
. 3.6.
60
2 , - , , , , , , , 59 -
47
( 3.6, . 3.5)
[469].
60 - 89%,
53.
. 3.5.
57
132
3.6
, 5 - , - , -
,
1 , 57 , ,
,
.
3.5 60
R1 R , (%)
59 C6H5 2 C6H5 60 67 59 4-C2H5OC6H4 2 3-FC6H4 60 92 59 2-FC6H4 2 C6H5 60 78 59 2-FC6H4 2 4-CH3C6H4 60 58 59 2-FC6H4 2 4-BrC6H4 60 62 59 2-FC6H4 2 4-ClC6H4 60 69 59 2-FC6H4 2 4-NO2C6H4 60 89 59 2,6- -FC6H3 2 2- CH3O-5BrC6H3 60 75 59 2,3- -ClC6H3 2 4-ClC6H4 60 70 59 2,3- -ClC6H3 2 2- CH3O-5BrC6H3 60 76 59 2,4- -ClC6H3 2 4-ClC6H4 60 62 59 2,4- -ClC6H3 2 4- CH3C6H4 60 80 59 2,4- -CH3OC6H3 2 4-ClC6H4 60 68 59 3- C6H4 2 3-FC6H4 60 55 59 3-FC6H4 2 4-CH3OOCC6H4 60 81 59 2,4- -ClC6H3 2 2-FC6H4 60 64 59 N-( H2)2- 2 2- CH3O-5BrC6H3 60 72 59 N-( H2)2- 2 4-ClC6H4 60 73 59 CH3 2 4-ClC6H4 60 81 59 (CH2)4CH3 2 4-ClC6H4 60 54 59 (CH2)4CH3 2 2- CH3C6H4 60 62
133
1 ,
60 - , -
, , ,
57 ( . 3.4).
-60 -90 ° 60 - ,
- N- , ,
.
60a, (R1 = C6H5, 4-C2H5OC6H4) ( -
60 ° 160 ° ) ,
60 (R1 = 2,6- -FC6H3),
.
EXSY ,
- ,
.
60 - , -
1 - ,
, .
3.6
60 -
R 1H , / 1S , / · 1G , /
60 H 68 3.2 -48 7.8 82 5 60 CH3 72 2.8 -33 7.5 81 6 60 Br 69 3.6 -41 6.0 82 6 60 Cl 57 3.0 -80 8.6 82 5 60 NO2 80 3.8 -14 6.3 84 5
134
[470]. ( . 3.6)
, , ,
[471], , ,
, N- -
R1 (5 - ). ,
.
-
( . 3.7).
DFT- ( 3LYP/c -pvdz) ,
C-N, N- -
,
.
3.7 -
DFT ( 3LYP/cc-pvdz)
N
O O
FN
O O
N
O O
FA
E /
A 57,02
116,77
52,59
,
N-
,
135
, .
.
N- - 5 -
,
,
( . 3.7).
3.2.
,
,
. - ,
[472, 473],
. - , ,
,
[474, 475], [476], [474]
[477-480]. ,
,
[481, 482].
-
,
[483-485].
61 - 3- -1,2,4- 5-
. , 5 5- -4-
18 ,
(120-200 ° )
136
( , , , )
,
. ó
–
.
,
3- 5-
13 - , , 2 , , , , , , , , , ,
61 -
( 3.7, . 3.8).
3.7
-
, 4-
5- ( 13 , , )
62 - ,
( 13 , ) 63 - [486, 487].
, 62 - 50-
55%,
.
137
63 , , ,
62 -
( 3.7, . 3.8).
4-
2 , 5- -3- -1- 13
61 –
-
– [3,4-b] -5,5'- 64 .
3.8 62 63
R2 R3 R1 X R (%)
13 CH3 C6H5 61 H O 2 4-C2H5C6H4 62 95 13 CH3 C6H5 61 H O 2 4-CH3SC6H4 62 60 13 CH3 C6H5 61 H O 2 4-NO2C6H4 62 95 13 CH3 C6H5 61 H O 2 4-CNC6H4 62 90 13 CH3 C6H5 61 H O 2 4-CH3OC6H4 62 75 13 CH3 C6H5 61 H O 2 2,4,5- CH3OC6H2 62 85 13 CH3 C6H5 61 H S 2 4-C2H5C6H4 62 65 13 CH3 C6H5 61 H S 2 4-ClC6H4 62 55 13 CH3 C6H5 61 H S 2 3,4- HOC6H3 62 50 13 CH3 4-NO2C6H4 61 H O 2 4-ClC6H4 62 55 13 CH3 CH3 61 H O 2 4-CH3OC6H4 62 50 13 CH3 CH3 61 CH3 O 2 4-CH3C6H4 62 50 - CH3 H - H O - 4-C2H5C6H4 62 85 - CH3 H - H O - 4-CNC6H4 62 90 - CH3 H - H O - 4-ClC6H4 62 90 - C6H5 H - H O - 4-BrC6H4 62 90 13 CH3 H 61 H O 2 4-C2H5C6H4 63 85 13 CH3 H 61 CH3 O 2 4-CH3SC6H4 63 50 13 CH3 H 61 H O 2 4-NO2C6H4 63 75 13 CH3 H 61 H O 2 4-CNC6H4 63 85 13 CH3 H 61 H O 2 2,4,5- CH3OC6H2 63 70 13 CH3 H 61 H O 2 3,4- HOC6H3 63 55 13 CH3 H 61 H O 2 3-C2H5O -2-HOC6H3 63 90 13 C6H5 H 61 H O 2 4-ClC6H4 63 75 13 C6H5 H 61 H S 2 4-ClC6H4 63 55 13 C6H5 H 61 H O 2 4-BrC6H4 63 75 – – 63 , , ,
,
, 5-
,
. ,
138
, ,
.
,
N- 13 , ,
, ,
, , .
N- ( )- 5- 13 , ,
, , . ,
170 °
. ,
,
190 ° ( . 3.8).
: 5- 13 - ,
61 - 2 , , ,
,
64 - ( , 3.8, . 3.9). ,
, ,
[488, 489].
R4 R5
.
64 , , R4 R5,
,
65 , 66 ,
139
3
( , 3.8).
,
65 , 66 ,
.
64
.
3.8
, 66 - ,
61 - 2 , , ,
3 ( )
33 , - .
–
65 - ,
13 - 2 , , ,
. , ,
140
,
.
, ,
,
,
64,
.
3.9 64
-
R1 X R2 R3 R4 R5 (%)
2 + 13 + 61 H O CH3 C6H5 4-CH3SC6H4 64 95 2 + 13 + 61 H O CH3 C6H5 4-CH3OC6H4 64 98 2 + 13 + 61 H O CH3 C6H5 4-ClC6H4 64 80 2 + 13 + 61 H S CH3 C6H5 4-ClC6H4 64 82 2 + 13 + 61 CH3 O CH3 H 4-CH3OC6H4 64 80 2 + 13 + 61 CH3 O C6H5 H 4-CH3OC6H4 64 63 65 + 66 H O CH3 H 4-C2H5C6H4 4-CH3OC6H4 64 75 65 + 66 CH3 O CH3 C6H5 4-CH3SC6H4 4-CH3OC6H4 64 60 2 + 61 + 66 H O CH3 C6H5 4-CH3SC6H4 64 70 2 + 61 + 66 H S CH3 C6H5 4-ClC6H4 64 70 2 + 61 + 66 CH3 O CH3 H 4-CH3OC6H4 64 55 2 + 61 + 66 CH3 O C6H5 H 4-CH3OC6H4 64 55 2 + 61 + 66 H O CH3 H 4-C2H5C6H4 4-CH3OC6H4 64 65 2 + 61 + 66 CH3 O CH3 C6H5 4-CH3SC6H4 4-CH3OC6H4 64 55 2 + 13 + 65 H O CH3 C6H5 4-CH3SC6H4 64 75 2 + 13 + 65 H S CH3 C6H5 4-ClC6H4 64 78 2 + 13 + 65 CH3 O CH3 H 4-CH3OC6H4 64 53 2 + 13 + 65 CH3 O C6H5 H 4-CH3OC6H4 64 54 2 + 13 + 65 H O CH3 H 4-C2H5C6H4 4-CH3OC6H4 64 65 2 + 13 + 65 CH3 O CH3 C6H5 4-CH3SC6H4 4-CH3OC6H4 64 55 –
, 64
-
. , 64 ,
6-12
62 63 ( 3.8). ,
, ,
141
61 2 5- 13
, ,
64, – 62
63, R3.
3.3. 6-
3.3.1. 1,3-
1
6-
1,3- [378-381].
,
, , ,
.
[490, 491]
,
68 ( 3.9).
3.9
6-
67 - 47
2 , , , , - - .
68 - :
142
10 150 °
Et3N [492].
3.10 68
6- (%) R1 X R
67 H S 2 4-CH3C6H5 68 92 67 H S 2 4-CH3OC6H5 68 90 67 H S 2 2-CH3OC6H5 68 91 67 H S 2 4-FC6H5 68 90 67 CH3 O 2 4-CH3C6H5 68 93 67 CH3 O 2 4-CH3OC6H5 68 94 67 CH3 O 2 2-CH3OC6H5 68 93 67 CH3 O 2 4-FC6H5 68 90 67 H NH 2 4-CH3C6H5 68 93 67 H NH 2 4-CH3OC6H5 68 88 67 H NH 2 2-CH3OC6H5 68 95 67 H NH 2 4-FC6H5 68 90
68 -
, (10 120
), ,
, 88-95% ( 3.9, . 3.10).
,
68.
71, 5 10
.
,
,
57 60.
( 3.10), ,
65 59
1,3- 47 (" "), 2
143
61 69 (" ") N- 6-
70 47 (" ").
3.10
,
,
5,10-
71. , ,
,
71.
3.3.2.
6-
, ,
. [493, 494]
N- - N,N'-
6-
10 90 %. , [494]
144
,
[493] , N,N`- 6-
.
74 N,N`-
6- 67 , .
74 ,
[493, 494],
(120 – 200 ° ) -
73 , (
3.11).
3.11
73 , 72 ,
150 °
1
74 - 15 30%, , ,
.
190 °
74, 73.
6- 67 , 2 , ,
75 -
145
,
80 – 200 °
73 - ,
[2,3-d] 78 ( I, 3.12).
3.12
78
,
- –
76 - ( II, 3.12).
6-
67 , ,
[495].
, ,
. , (10-20 )
6- 67 , , - 76 -
146
. ( 2- )
[2,3-d] 77 - , 5,8-
78 - ~ 3:2.
6 - 10 ,
,
77 - 78 - .
3.11
77, 78 R R1 X , %
77 H H 75 77 Cl CH3 69 77 H H S 60 77 H Cl S 66 77 CH3O Cl S 52 77 (CH3)2N Cl S 65 77 NO2 Cl S 40 77 H F S 58 77 F COOCH3 S 52 78 Cl Me O 78 78 H Cl S 58 78 CH3O Cl S 52 78 (CH3)2N Cl S 67 79 - H S 74 79 - Me S 68
67 , 76 , -
ó ( , ),
[2,3-d] 77 , , -
( 40 – 75%, . 3.11),
76 -
77 78.
,
67 , 76 -
3-5 5,8- 78 -
52 – 78%. 76 , -
77 , , - .
147
, ,
5,7- [2,3-d] 77 78
, ,
: ó
, – . ,
,
- . ,
,
, ó
.
( . 2.1.1,
2.3).
,
:
[2,3-d]
, - .
76 , ,
,
79 , ,
( 3.12).
[496].
, [366]
78,
,
, ,
76 6- 67,
78, , ,
148
. ,
, ,
78 -
[2,3-d] 77,
.
78 - N-
3- - -
[2,3-d] 77 , - (40-65%).
77,
67 -
76 N- ( 3.13).
3.13
3.4.
.
, CH-
( 2.3), – ,
( )
( ).
149
3- 5-
( 3.14), –
.
13, - 47 2
3
VII, ,
, 49.
,
VIII ( ).
,
1 2, VIII.
150 ° , ,
, ( . .
3.3).
, ,
- ,
« » VIII
( 2). - -
, , ,
, 48 50.
1,
( - )
50.
,
,
3
150
- [497, 498]:
1,3- VIII,
, (VIII
X), 50.
3.14
,
5- –
3-
, 3-
.
18,
,
VIII,
151
(
3.15).
3.15
, 54 ( )
,
XIII, VII,
3- 5- 13 (
3.14).
,
( XI), 1,3- 47
, , ,
55.
,
, ,
57.
152
ABCC ,
,
[113]. , ,
XIV, XV
XVI.
61, 2 5-
13
. ( ,
3.16)
XVII XVIII, ,
, [4+2] ,
64.
3.16
, ,
XVII,
, XVII
XIX XX 63 ( , 3.16). R = CH3, C6H5,
4-NO2C6H4
63,
62.
153
,
VII, VIII, XIII, XX ,
. , [357, 499]
, ,
,
XXI XXII ( , 3.17),
XXIII .
,
- XXIII
( ) [344-347].
O
O
R O
O
O
R
X
Y NH2
O
O
R
HN Y
X
X
NH
Y
R O
OH
O
O
X
Y NH2
O
R O X
NH
Y
R O
OHOH
YX
XXI XXII
XXIII
A
3.17
* * *
,
,
,
- ó ,
.
154
,
,
[5,1-b] [3,4-b] -5,5’-
( ), [3,4-b]
[4’,3’:4,6] [2,3-d] ( ).
,
5- 1,3-
:
; ( ,
- ) ,
[4,3-c] :
[5,1-b] .
. 3.7.
155
5- -N-
-4-
[1,5-a]-
.
( . 3.7).
,
-
, ,
, , .
156
4
-
: ,
- ,
- ,
.
. -
, -
,
.
-
,
-
( I- II- , 4.1).
4.1
, 1,2,5,6- ,
-
( ) ( ), -
. ,
, ,
, ,
157
, ,
- .
4.1. 1,2,5,6-
4.1.1. 1,2,5,6-
, , [500],
[501], [502],
.
.
, 1,2,5,6-
, ,
–
. , 1 (
4.2), 79
,
80 [503, 504]. ( 2),
[505], 82
, - 81.
3, -
83 [506], ,
« » . ,
(R1 = R2 = H) ,
84, 85,
.
158
4.2
1,2,5,6-
4,
-
[507].
.
,
, -
, ( 4.3,
. 4.1).
87 -
2 , , , , , , , , ,
24 – 48 ,
89 - ,
2, 4 6 [508].
159
4.3
. , - , -
87 ,
N,N -
- - 90. ,
, - ,
( , -2- -3- ,
2- , 2- , 3- ),
.
,
. ,
–
.
.
, - 87 ,
-2- 2 .
.
5 .
4.1
89
92
-
R
1 R
2
R3
R4
R5
, %
,
%
87
2-H
OC
6H4
4-FC
6H4
2
H
H
- 89
80
-
87
C6H
5 2-
HO
C6H
4 2
C
6H5
H
- 89
85
60
87
2-
HO
C6H
4 -C
5H4N
2
4-
ClC
6H4
H
- 89
85
84
87
3,
4-O
CH
2OC
6H3
2-O
H-5
-ClC
6H3
2
4-B
rC6H
4 H
-
89
85
90
87
4-C
H3C
6H4
2-H
OC
6H4
88
CH
3 C
H3
- 89
80
- 87
C
6H5
2-H
O-5
-ClC
6H3
2
-C4H
3S
H
- 89
85
70
87
2-H
OC
6H4
2-H
OC
6H4
2
-C4H
3S
H
- 89
85
72
87
C6H
5 2-
HO
C6H
4 2
-C
4H3S
H
-
8980
75
87
C
6H5
2-H
OC
6H4
2
-(2-
CH
3C4H
3S)
H
- 89
75
70
87
2-H
OC
6H4
2-H
OC
6H4
2
-C6H
4N
H
- 89
90
98
87
3-B
rC6H
4 4-
CH
3OC
6H4
2
4-H
OO
CC
6H4
H
- 89
90
61
87
4-
CH
3OC
6H4
4-C
H3C
H2C
6H4
2
4-C
lC6H
4 H
-
8995
72
87
C
6H5
C6H
5 2
4-
ClC
6H4
H
- 89
95
65
87
3-B
rC6H
4 4-
CH
3OC
6H4
2
4-C
lC6H
4 H
-
8995
95
87
3-
BrC
6H4
4-C
H3O
C6H
4 2
4-
CN
C6H
4 H
-
8995
91
87
3-
BrC
6H4
2-H
OC
6H4
2
4-C
lC6H
4 H
-
8954
90
87
4-
CH
3C6H
4 2-
HO
C6H
4 2
3,
5-C
lC6H
3 H
-
8955
89
87
4-
CH
3OC
6H4
2-H
OC
6H4
2
2-C
H3C
H2O
C6H
4 H
-
8957
67
87
4-
CH
3OC
6H4
2-H
OC
6H4
2
4-C
lC6H
4 H
-
8952
92
87
4-
CH
3CH
2C6H
4 2-
HO
C6H
4 2
2-
CH
3O-5
-BrC
6H3
H
- 89
54
70
87
4-C
H3C
6H4
2-H
OC
6H4
2
4-B
rC6H
4 H
-
8965
91
87
4-
CH
3CH
2OC
6H4
2-H
OC
6H4
2
4-C
lC6H
4 H
-
8960
92
87
4-
ClC
6H4
2-H
O-3
-CH
3OC
6H3
2
3-C
H3O
C6H
4 H
-
8956
55
87
4-
ClC
6H4
2-H
O-3
-CH
3OC
6H3
2
3-FC
6H4
H
- 89
53
85
87
4-C
lC6H
4 2-
HO
-3-C
H3C
H2O
C6H
3 2
2-
FC6H
4 H
-
8951
80
87
3-
CH
3OC
6H4
2-H
O-3
-CH
3CH
2OC
6H3
2
4-FC
6H4
H
- 89
55
70
87
4-C
H3C
H2C
6H4
2-H
O-5
-ClC
6H3
2
4-B
rC6H
4 H
-
8960
99
87
4-
CH
3OC
6H4
4-H
OC
6H4
2
4-C
lC6H
4 H
-
8925
60
87
C
6H5
C6H
5 2
C
6H5
H
- 89
55
80
87
2-H
OC
6H4
2,5-
CH
3OC
6H3
2
4-C
H3O
C6H
4
- 89
85
71
159
4.1
()
-
R
1 R
2
R3
R4
R5
, %
,
%
87
C6H
5 2-
HO
C6H
4 2
4-
CH
3OC
6H4
-
89
85
55
87
C6H
5 2-
HO
C6H
4 2
3-
NO
2C6H
4
- 89
75
54
87
2-
HO
C6H
4 2,
5-C
H3O
C6H
3 2
4-
ClC
6H4
-
89
85
55
87
2-H
OC
6H4
2,5-
CH
3OC
6H3
2
C6H
5
- 89
85
55
87
C
6H5
2-H
OC
6H4
88
CH
3 C
H3
- 89
83
-
87
C6H
52-
HO
C6H
4 91
-
- C
6H5C
H2
9285
-
87
2-H
OC
6H4
2-H
OC
6H4
91
- -
CH
(CH
3) 2
9285
-
87
2-H
OC
6H4
2-H
OC
6H4
91
- -
CH
3 92
90
- 87
2-
HO
C6H
4 2-
HO
C6H
4 91
-
- C
2H5
9275
-
87
2-H
OC
6H4
2-H
OC
6H4
91
- -
CO
OC
2H5
9295
-
87
2-H
OC
6H4
2-H
OC
6H4
91
- -
CH
3CO
92
90
-
–
; -
159 159 159 159 159 159 159 159 159 160
162
,
5
89 , 90
90%, .
, 90
5% ( . 4.1) [509].
0 5 10 15 20 25 30 35 40 45 50 55 60 65 70 75 80 85 90 950
10
20
30
40
50
60
70
80
90
100
, %
,
. 4.1. 87 , -2- 2
.
. ,
.
90.
87 , , , - ,
(2 , - ) (2 ) .
, - 87 , -
163
91 - 92 - ( 4.3),
.
- , -
( 87 ). OH-
( 87 ) ,
89 , . ,
- ,
,
.
89 R3 R4
- - . , ,
1 ( . 5.3),
( . 4.2),
.
. 4.2. 89
,
. ,
.
164
1,2,5,6- .
,
, , S-
[510, 511].
,
. in situ
(4- ).
S- 93
1 , , .
, , 4.2
( ).
, 87 S-
40 100 . %
, 20 0 . %
.
.
89 , , .
87 , -
, S-
- - ,
, ,
94.
87
2 ( . 4.3). ,
95 ( 4.4).
165
4.2 3 , 3 , 3
S-
S- , .% ( )
, %
R3 = 4-CH3OC6H4 100 80 60 40 20 0
100 100 100 100 88 71
S- , .% , %
R3 = Ph R3 = 4-CH3OC6H4 100 80 60 40 20 0
75 65 65 62 62 60
70 65 65 65 60 55
,
95, - 87 4-
2
96 , .
,
89
,
( . 4.3).
166
4.4
4.3
94, 96 , -
,
. %
, %
94 40 55 94 60 60 94 80 60 96 40 50 96 60 60 96 80 60 96 40 62 96 60 65 96 80 62
,
, S-
, -
, ,
,
[512],
, - .
S- .
,
1,2,5,6-
, ,
87 ,
167
.
,
243-245 ( 1.58).
4.1.2. 1,2,5,6-
, , .
1,2,5,6- 89 92,
. ,
.
NH-
, 1,3-
. -
[3].
1,2,5,6-
97 ( . 4.3)
-
. ,
, -
,
98 99.
. 4.3. 1,2,5,6-
168
6- -
87 .
,
- - .
, 87
,
-
97 –
.
.
( )
(30–50 ° ), , ( 120 ° ),
.
,
, ,
.
87
.
,
,
, ,
.
.
169
( 4- )
: 89
8- .
,
. ,
=N / NH- ,
( 4.5).
[513, 514].
89 2
( . 4.4).
0 ° ,
.
4.5
, AlCl3 TiCl4 -78 °
72
170
-
89 2 .
72 -78 ° ,
, 12 ,
0 ° .
ZnCl2 BF3*Et2O
6- ,
- 1
.
-78 25 ° Yb(OTf)3, Cu(OTf)2,
BF3*Et2O.
4.4 -
87 2
, °
, . AlCl3 -78 72 CH2Cl2 0.1
TiCl4 -78 72 CH2Cl2 0.1
AlCl3 -78 … 0 3 -78 ° , 12 0 °C CH2Cl2 0.1
TiCl4 -78 … 0 3 -78 ° , 12 0 °C CH2Cl2 0.05
ZnCl2 -78 … 0 3 -78 ° , 12 0 °C CHCl3 0.5
LiBr -20 … 25 4 -20 ° , 12 25 °C CH3CN 1.0
Yb(OTf)3 -15 … 25 3 -15 ° , 6 25 °C CH3CN 1.0
Cu(OTf)2 -15 … 25 3 -15 ° , 6 25 °C CH2Cl2 1.0
BF3*Et2O -78 … 25 3 -78 ° , 12 25 °C CH2Cl2 1.0
BF3*Et2O -78 … 25 3 -78 ° , 12 25 °C DMF 1.0
BF3*Et2O -78 … 25 3 -78 ° , 12 25 °C CH3CN 1.0
,
,
171
.
89 - 2
. 30
, ,
97, - -
89 ( 4.6). ,
2 , , , ,
.
4.6
,
, .
=N ,
, , 100 -
( 4.7) 76-87%.
, 1,2,5,6-
89 , (R3 = R4 = CH3)
100 -
101 (102).
172
4.7
,
89 , , ,
,
100
( 4.7).
.
4.2. -
- , 3,5a-
[1,2-c] 103, 1,3,4,6a- [1,2-a]-
104 1,1 - [1,2- ] 105 ( . 4.4),
.
173
. 4.4. -
-
, ,
,
.
, ,
,
, ,
, .
,
[515].
103-105
,
- ,
= - 1,4-
( II-M, 4.1).
1.3.1,
[423, 427].
4.2.1. -
[252, 253, 258]
4- 2 - 106
174
111-113,
( 4.8). - 109
114.
, -
107, 108
. ,
.
4.8
111-114 -
,
, ,
.
,
,
.
10% [516].
[517].
175
, - ,
,
, . ,
, .
–
-
[518].
, -
Ni (II)
1972 [519, 520].
[521-526],
,
[527] -
.
,
,
, Ar-Ar
-
.
Ar-Ar - ,
, – B(OH)2.
,
,
, .
176
[1,1’- -
( ) ] (II) (PdCl2dppf) ( . 4.5),
.
-
. ,
104 105 ( . 4.4), ,
60 [528],
[529, 530]. ,
(10-20 ),
1-2 .
, , , ,
.
, ,
.
-
-
115 ,
, 116 (
4.9). - :
-
PdCl2dppf CHCl3 (1:1).
,
117 30 ,
(
~70%).
. 4.5. [1,1’- -( ) ]-
(II) (PdCl2dppf)
177
.
115
.
4.9
( – SDS),
-
[531] [518, 532]. ,
,
-
, ,
( ) .
, SDS (1% )
5
98%,
( ) 117
95%
( ).
116 ,
117 , ( 4.10). ,
:
119 2 – 121.
- ( ) - ( )
178
120, 121
.
121 121
,
120.
4.10
:
122 116 123
( 4.10).
124
179
125
( 30%).
124 -
,
-
.
( 69 °C), -
, .
,
, 20
.
.
128 - 127 -
4- -1,2- 126 ( 4.11). , -
126,
[260],
.
, [260],
128 - . ,
75:25,
,
( . 5.3) 5-
( ) 6- 128.
A 128 - -
,
180
.
4.11
128 - ( + ) -
116 ,
- ,
129 - ( 4.11)
[518]. , 128
.
- ,
,
.
181
4- - 4,5- -1,2-
- [533].
1,2- 130 , 2,3- -1,3-
-1- 127 - 2- -3-(4- )-1- -2-
-1- 132 c 16 – 43%
131 - ( 4.12).
4- -1,2- 130
127 -
, 128 - ,
, 1 ,
, -
( . 4.5).
4.12
-
1,2- 126 130 ,
,
-
. 4- -1,2-
126 ,
130 ,
126
( 4.11 . 4.5).
182
4.5 131 -
, %
R1 R2 R 130 CH3 CH3 127 H 131 45 - - 130 CH3 CH3 127 Br 131 45 - - 130 CH3 CH3 127 F 131 39 - - 130 CH3 CH3 127 CHF2O 131 30 - - 130 CH3 CH3 127 C5H11 131 39 - - 130 CH3 H 127 H 131 38 66 34 130 CH3 H 127 Br 131 43 60 40 130 CH3 H 127 C2H5 131 26 66 34 130 CH3 H 127 C5H11 131 30 55 45 130 CH3 H 127 F 131 37 60 40 130 CH3 H 127 C6H5 131 16 55 45
( . 4.2.2)
133-135,
, ( 4.13).
4.13
,
- , ,
, ,
,
[252, 258, 534].
183
,
.
(N- ,
- ),
( ) .
N- ,
[252],
,
[1,2-c] -6,8- .
( )
– 20
.
.
. ,
136
,
. 136 N-(4-
) 137
, , ,
22% 139 ( 4.14).
4.14
184
138, -
, ,
.
[258, 534], , ,
. ,
131 , , 4- 2
141 - ( 4.15) [533].
NN
O
R2 R1
O2N
O2N
141 -
R
NN
O
R1 R2
O2N
O2N
R
A
NNO
O2N
O2N
NN
R2 R1
O2N
R
+
R3
O
131 , ,
+
R1,R2
R
2
,
140
NN
NO2
R
NN
O
R
NO2
H
H
H
R3
HH
R3
131 -
+
O
2 ,
,
141 -
N OO NN
R
R
NO
OR3
R3
HH
H
H
131 - +,
137 , 142 -
H H
H H
H H
1 3a1 3a
H H
1 3a
10
9a6b
6a
4.15
7,8- 131
141 ,
131 , ,
, 141 ,
( 4.15, . 4.6).
185
4.6 141 142
, %
R R1 R2 R3 131 H CH3 CH3 2y NO2 141 39 - - 131 H CH3 H 2 NO2 141 31 60 40 131 H CH3 H 2 NO2 141 53 60 40 131 H - - 2 NO2 141 78 - - 131 C2H5 - - 2 NO2 141 77 - - 131 Br - - 2 NO2 141 78 - - 131 H - - 2 Br 141 29 - - 131 C2H5 - - 2 Br 141 82 - - 131 Br - - 2 Br 141 78 - - 131 H - - 137 F 142 53 - - 131 C2H5 - - 137 C2H5O 142 68 - - 131 Br - - 137 C2H5O 142 66 - - 131 C2H5 - - 137 C2H5O 142 61 - -
1 ( . 5.3)
, 1 3 141
.
, - 131
-
, , , - .
,
-
, ,
, , . .
-
.
131 -
2 , - 1 3
141 - ( 4.15).
131
140,
186
,
, .
131 -
N- 137 ,
142 - ( 4.15)
6b 9 ,
. ( 6
10) - ,
- -
. ,
.
, 5
, N-
4- ,
–
.
131 - N- 137 -
90 50-60%
143 - ,
( 4.15).
N-
: 131
N-(4- ) 137 , 20 °
, (~7%) 142 .
,
-
- ,
,
.
187
-
. , 131 ,
6-12 , ,
,
.
,
,
:
143
144 ( 4.16).
4.16
[535, 536].
4.2.2.
,
,
,
-
.
, 4-
, .
,
188
.
[537]
[538].
,
[251].
,
,
.
,
– .
4.2.2.1.
, ,
, .
4.17
189
,
, 131 ,
2 , N- 137 , , 25-35 °
( )
141 , , , 142 - ( 4.17, . 4.7),
,
( 4.15, . 4.6).
4.7 141 142
, % R R3
131 C2H5 2 NO2 141 68 131 Br 2 NO2 141 77 131 C2H5 2 Br 141 78 131 Br 2 Br 141 69 131 C2H5 137 C2H5O 142 61 131 Br 137 C2H5O 142 68 131 C2H5 137 C2H5O 142 64
, ( ,
)
N-
1 3 6 10, .
136
N- 137 5 ,
, , ,
6 ,
.
, , ,
, - ,
, ,
4.6 ).
. 4.6. ( )
(0 –
,
.
,
,
)
,
O2N
,
,
,
,
600
,
1 – 7
92
NN145
190
,
5-7
2
N
(
7
.
) ( )
(0 –
,
145
. 4.6
)
, 1 –
.
,
.
max ~
),
,
– 7
( . 4.
( .
450 ,
,
92
).
6 ),
.
.
,
,
191
, 147
, ,
,
.
,
( ) ( )
.
,
.
, -
4-
-
, ,
.
- ,
. ,
(-95 ° -113 °
) ,
- .
,
,
- ( max ~ 450 ).
,
[248].
-
. 4
(1 –
15 ;
,
.
4
.
,
4.7.
145
,
4.2.2.2.
,
1-2
;
–
,
145,
(
2 –
192
,
,
,
.
-
,
).
15
( . 4.
).
,
5
max 5
2).
,
6),
, . .
,
1%
31
571
(
,
,
,
,
3
. 4.7,
,
,
,
193
, ,
, .
-
, 145 (
UB3LYP cc-pvdz [539]), 412
,
(~570 ).
. 4.8.
,
( . 4.8)
.
4.2.2.3.
( ), . .
, ,
,
.
,
( ), ,
(
). ,
194
,
,
.
+ 1,5% 145
(365 , 1 , 20 ° )
,
~630 .
,
.
630
400 ( - ) [540].
+ 1.5% 145
, ,
, 2
145 .
,
.
,
.
133,
.
133
.
. 4.9
+ 1.5% 133,
.
,
–
38.4 °
133
,
O
O
1.
35.7 °
,
.
3 145
1
–
133
5% 133
.
5
–
133 1
146
195
-
46
.
133
(Ch
.
14
146.
. 4
SA),
,
13
46.
,
,
4.9.
(1
33
,
1) +1,5%
7
% 133 (2)
. 4.
+133
( . 4
1
1.2
1.4
1.6
1.8
2
2.2
2.4
400
D
.10. ( )
+1
, 3 – 3
).
+
,
.
,
4.10 ),
500
,
)
33
, 4 – 16
3
+133,
.
,
,
+
600
, nm
1
2
4
430 (
65
(0 –
, 4
+133
700
3
196
. 4.10
(1 –
– 5
.
800
~6
).
); ( )
, 1 –
,
,
,
~450
+133
630
)
, 2 – 1
30
5 – 60
,
.
, 2
30
,
, 3 – 45
2 – 1
630
0 ,
.
5
.
197
, , .
, ,
,
.
,
133
, ,
.
630 450 ,
, ,
. 4.10
,
, , ,
. ,
450 :
536 495 ( 1-4),
– 529 ( 5).
,
max ~ 450
(
)
, . ,
[541]
[542]. ,
,
133,
. , 133
198
: <
< .
4.2.2.4.
-
, , ,
,
, 450 .
, ,
,
.
-
,
.
, , -
(365 ) 4-
- ,
,
~10-20 .
98%
2% . , « »
,
4.2.2.1.
132 , N-(4- ) 137
,
199
141 ( . 4.15 4.17). N-
132
,
2 0.5 – 0.7%,
. ,
132 -
365 ,
N-(4- ) 137 .
141 2.8%.
~0.7%.
,
2 – 2.5%,
, .
,
.
[537, 543] .
-
,
,
200
.
.
,
.
( ),
[544].
- 136, 132 145
, .
,
6-10 , 12-24 , 2
.
, – ,
, , ,
,
–
-
.
- 145 (
UB3LYP cc-pvdz) [539], , max
~590 ,
.
, ,
[249] [537]
,
201
. ,
,
.
- .
131 , 136 145,
, ,
.
, -
145 , -
-
,
( . 4.11 ).
, 136,
, (g=2.0039),
,
,
, ( . 4.11 , ).
131 ,
( . 4.11 ).
136
5
.
.
, -
,
.
– 5
-0,6-0,3
00,30,6
32
-2
-1
0
1
2
3
-4
-3
-2
-1
0
1
2
3
4
3
. 4.11. ( )
230 328
3230 328
3230 328
, 4 – 10
1
80 3330
80 3330
80 3330
)
)
)
)
36; ( )
3380
3380
3380
202
136: 1 –
; ( )
3430
3430
3430
131 ;
3480 B,
3480 B,
3480 B,
, 2 –
– 2
145; ( )
, 3
-
-
203
,
, ,
,
.
–
136 ,
20
50%.
-
, ,
,
( . 4.12). ,
,
, :
[537, 545].
. 4.12.
4-
( .
4.12), , [546],
204
[538], ,
.
- , , ,
, ,
, ,
, .
( . 4.13)
,
,
« » .
. 4.13. -
, :
1) « » ,
, ,
;
2)
,
. ,
- (ab initio, UB3LYP, cc-pvdz) ,
( . 4.14);
.
cc-pvd
3
4
1,2,5,6
4.15).
) . 4.14.
); ( )
dz); ( )
3)
4)
;
5)
.
6-
2
C=N
205
) 145: ( )
;
* * *
-
2,(2),4,6-
1,5,9-
.
( )
-
(ab
(ab initio
(
[5.5]
) (
b initio, UB
o, UB3LYP,
)-
-1-
.
(
B3LYP,
, cc-pvdz)
-
( .
-
.
206
. 4.15. -
-
-
(1,2- )
, , -
.
,
.
-
, , ,
,
( . 4.15).
207
5
, - ,
- ,
,
- .
,
,
.
5.1. , 2
3- -1,2,4- 5 ,
3 - ( 2.1), ,
,
.
. 5.1. 1 7 8
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0PP
M
0.69
0.25
0.36
0.62
2.12
2.05
1.00
0.66
0.34
3.00
***
*
**
*
**
(*+**)
(*+**)
N
NH
N
NOH
ON
NH
NN
OH
O+
O O
7 (*) 8 (**)
7.0 6.5 6.0 5.5PP
M
2.12
2.05
1.00
0.66
0.34
***
(*+**)
(*+**)
208
1 ( . 5.1) 13 ,
- , ,
- ( . 5.2),
1 ,
, .
. 5.2. 3 3- -1,2,4-
5
, [340, 343, 344],
1H :
9.5-10.5,
,
2 . . , 7
8 - NH
,
SY. ,
.
–
R1 ( CH3S), -
. 5
7
)
)
)
5.3.
7,
7 (
7
17
24
. 5.3 ).
)
)
41
209
R.
)
)
)
) 7
9
19
29
41 7 , 9 , 11
8 ( . 5
)
)
)
, 17 , 19 , 2
.2)
,
,
23 , 24 , 29
– .
11
23
38
9 , 38
.
210
6, 14-17, 19, 28, 29, 31, 32, 38, 42, 44, 45,
( . 5.4) ( . 5.3 , , , ).
. 5.4. (1D ROESY)
14, 15, 16, 17, 19 38.
20,
2 5- 18
( 2.4),
19, - ( .
5.5), COSY,
ROESY, HSQC HMBC.
. 5.5. 3 5-
18 ROESY ( ) HMBC ( ) 20
211
,
20 5.5,
.
,
11 ( . 5.3 ).
24, 26, 30,
9, 23, 25, 41 39,
,
, 1D 2D ( .
5.3 , , ).
, 1 13
39
- ( . 5.6),
COSY, HSQC, ROESY HMBC.
NN
N NH
R1
O
H
H
ON H
SR3
HH
X
R2
X
NN
N NH
H
HO
H
ONH
S
R2H
R3
NN
N NH
H
HO
H
ONH
S
R2
R3
) ) )
NN
N NH
R1
HO O
NHS
R2
R3
NN
N NH
O
NHS
R2
R3
R1
OH
NN
N NH
R1
HO O
NH
R2
S
NN
N NH
O
NH
R2
S R1
OH
R3 R3
. 5.6. ROESY ( )
HMBC 6 ( ) 5 ( ) 39.
.
ROESY S-
R1 ( ) , HMBC
212
R1
, ,
. , HMBC,
, 5 6 ( .
5.6 , ), .
39
- 5
6, (3J = 11.5 – 12.5),
ROESY ( . 5.6 ),
(
, )
- .
, ,
-
. ,
23
( . 5.7 ).
N
NH
N
NH+
OH-OOCPh
OMe
N
NH+
N
NH
OH-OOCPh
OMe
N+
NH
N
NH
OH-OOCPh
OMe
NNH
N
NH+
O Ph
OMe
O
O
H
) ) . 5.7.
23 ( )
-
- ( . 5.7 ) .
5.2. , 3
5- ,
-
213
48 49 ( 3.1). 1 13
,
- ( . 5.8 ).
, R3 = H ( 63, 3.7).
) 48, 49, 63
) 1 48 ) 1 49
) NOESY
48
. 5.8. 48, 49 63
-
1 , COSY
, , ( .
5.1).
1 ( . 5.8 , ),
NH- ( 48 63),
12.0 11.0 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0PP
MPP
M
12.5
57
9.89
1
7.53
97.
519
7.39
77.
377
7.35
67.
296
7.27
57.
255
7.03
27.
008
6.66
26.
638
5.28
5
3.60
3
2.44
32.
369
2.32
32.
163
2.11
81.
971
1.92
6
0.99
00.
833
0.99
0.99
2.06
2.02
1.01
2.02
1.99
1.00
3.01
1.07
1.00
1.00
0.98
3.00
2.93
7.0PP
MPP
M7.
539
7.51
97.
397
7.37
77.
356
7.29
67.
275
7.25
57.
032
7.00
8
6.66
26.
638
2.06
2.02
1.01
2.02
1.99
10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0PP
MPP
M
10.4
78
7.69
67.
661
7.35
67.
325
7.28
77.
236
7.03
06.
956
6.15
06.
127
2.60
12.
516
2.39
42.
251
2.18
42.
054
1.97
5
1.03
30.
915
0.98
2.10
3.12
4.16
1.99
0.99
1.01
4.05
1.00
3.20
3.00
7.5 7.0PPM
PPM
7.69
67.
661
7.35
67.
325
7.28
77.
236
7.03
06.
956
2.10
3.12
4.16
-
R2 (
. 5.
55
,
( . 5.10
6
.9.
)
-
( . 5.9
( .
0 ).
62
(
49.
,
9).
5.10 ).
(
55
214
2.
49),
NH-
55 (
.5 .
48 ( .
3.4):
1.5 .
54
55
.
( . 5
R2
5.8 )
.
,
62 (
5.10 ).
NOESY,
54
55
-
2.3 –
,
3.7) –
R
,
4
5
-
–
,
–
R
ROESY
)
. 5
13.0 12PP
MPP
M
12.7
920.
74
7.4PPM
PPM
7.37
2
) . 5.10.
-9-
Y ( . 5.
) 1H
5.11. 1
.0 11.0 10.0 9.0
7.2 7.0
7.35
4
7.06
57.
044
6.94
46.
923
6.87
76.
855
2.02
3.17
3.92
50
( . 5.
.11 ),
) 1
8.0 7.0 6.0 5.0
7.37
27.
354
7.06
57.
044
6.94
46.
923
6.87
76.
855
6.09
7
2.02
3.17
3.92
0.88
NN
NH
O6.8
) (
5a-
11 ),
50
4.0 3.0 2.0 1.
4.43
04.
413
4.39
94.
382
2.43
32.
392
2.34
62.
283
2.26
72.
246
2.23
02.
108
1.96
6
0.99
2.11
1.08
3.00
2.01
097
NOH
215
( ),
(
-4,5
(
0
50 ( )
-
.0 0.0
1.92
61.
880
1.80
51.
771
1.73
51.
172
0.96
0
0.97
3.00
3.00
)
,5a,6,7,8-
. 5.11
)
( )
( )
62
H
, ).
)
( )
)
HSQC, T
ROE
[4,3-c]- 1
TOCSY
ESY 50
50
-
ROESY
,
(
S = 0
(
, -
Y
.
,
0.75, =
.
(
50
.
,
50 ,
-
32.8 , =
1
64
13
65-66
[3,4-b]
[547]: S
= 25.8
,
,
-
. .
(
-5,
216
,
.
(
S = 0.67,
).
-
,
,
. 5.12)
,5'-
,
, .
= 42.5
)-2',4
. 5.
. 5.11 , )
, = 1.3
4',6'-
12.
64
,
),
64.
(
,
,
,
)
,
217
5.3. , 4
, -
, ( 4.3)
–
( . 5.13 ).
)
)
. 5.13. -
, ( ) 1 89
- ,
( ) 1 ,
ABM ( . 5.13 ),
.
-
, , 2 5,
16.0 15.0 14.0 13.0 12.0 11.0 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0
0.65
0.97
0.65
1.08
2.05
2.89
1.06
3.96
1.02
1.03
0.06
0.95
0.99
1.09
Hx HmNH
Ha
HbOH
OH
N
NH
HO
Hx
HaHbHm
N
HO
.
. 5.
(
,
,
( -
15.
)
OSY
-
R3
H
. 5.14.
4.2
( . 5
).
N
NH
R1
R2
HH
89
218
,
,
2 – 5.1
5.14),
2
(2
1,2,5,6-
5.15).
,
N
NH
R
R3
H
2-
70/3
,
-
: 3JA
NH
R1
R2
H
)-
30.
89
JAM 10 – 1
; 3JBM
,
89
(
-2-(
89
.
11
4.1 – 4.9
1,2,5,6-
. 2.3)
4,6- -
-2- )-
9 ( .
,
,
100
9
-
-
-
.
,
0
219
- 1 13
.
2, 4 6
100
NOESY ( .
5.16),
,
.
-
,
89 , ( 4.7)
,
100. OSY -
,
. O SY
: 2-
, 3-
- ( . 5.17).
) ) ) . 5.17. OSY ( ) O SY ( ) 101 ,
102 ( )
,
101, 102.
. 5.16.
NOESY -
100.
2 (
[548].
128 -
. 5
4.4),
,
,
,
, 129 -
(7.60 –
5.18.
111 (
,
-
131 -
– 7.15
)
,
-
1
8.20
. .)
,
220
,
NOE
,
( 4
3,3-
3,5a-
111 ( .
128 (
. . (8.4
ESY
,
.
4.8),
-5-(2-
-1H
. 5.18) [54
. 5.19)
) 7.8
C=N.
95,
94
,
,
)-
H-
49].
( .
1H.
5 . . (7.7
.
.
,
1-(4-
[1,2-c]
4.11
,
7 ),
-
4.2.,
-
.
111-114
,
)-
4.12).
A .
,
-
4
,
-
7.
C4H.
7.60
.
C4H
A
.28 . .
.
. 5.19.
0 . .
0.72.
C4H
A.
A
,
(4J = 1.8
7
C7H
C5H
C7H
-
221
A C7H
,
, 3J = 8
7.24 .
A
,
7.45
3.0 3.
1
5-
ó
C=N
.2 )
.,
A – 7
. .
.4 . .
12
1.8
6-
N
.15 . .
8.4
(J
8 .
7.60 .
:
7.31 –
= 2.7
128
.
C6H
8.2 ,
–
)
H
,
,
3.5 .
.
1
1
. ( . 5.
.
,
–
20).
12
. 5.21.
(
,
3.
29 - 1
1H
AB-
,
. 5.22).
222
1
.0 . ,
131 -
14
,
1H
41 - (
~6.3
140,
14
. 5.21)
,
,
14
41 -
. 5.20.
128
.
41
8
1
6b, 9
. .
. 5
O2N
O2
1
a 10
6
.23.
(
H
H2N
H
H
2.08
6.4
. 5.22.
,
3 ( 10
(4.0 –
6b-H
-
)
NN
H Ph
1416
141
7), 1H
,
6.3 .
9 - ,
141
223
O2N
O2N1
,
(
1,2-
5.23
14
). -
5.05 .
1
N
N
H
H
H6.95
H6.46
3
- -(4-
-3aH-[1
141
3).
42 - (
.
NN
H
H
H H2.23
7.32
Br
14
1,3]
. 5.24),
.
3
r
141
41 ,
),
)-4-
[3,2-a]
4
1H
4
8- -
-1,2- -
] -
( .
.
6a,
10-H.
4.0 4.15
H
4
-
-
-
.
,
.
5
.
. 5.25. ( )
,
.
( . 5.25
) NOE
,
,
5.24.
5 ).
ESY (ab i
224
10,
1H
142initio, HF/6-
,
,
; ( ) -311G**)
9 -
142 .
142
6
10,
NOESY,
)
, 6b 9 .
9 ,
90°.
142
.
,
225
, 6b c 9
6 , 10 9 .
, 6 , 6b 9
, 10
.
ab initio, HF/6-311G** [550] ( . 5.25 ),
NOESY .
226
6
,
. , ,
, in vitro
, , ,
in vivo .
,
,
.
6.1. 4
60
, , , , ,
, , , .
,
.
In vitro .
(10 μM). ,
,
.
4 Division of Cancer Treatment and Diagnosis of National Cancer Institute, National Institute of Health (USA)
227
in vitro
[551, 552, 553, 554].
(PG)
: ( ) 100( )Ti Tz xC Tz
, , Ti Tz
( ) 100Ti Tz xTz
, , Ti < Tz
: Ti – ; Tz –
; C –
;
. , 50%
(GI50; ( ) 100( )Ti Tz xC Tz
=50), ,
(TGI; Ti = Tz)
, 50%
(LC50; ( ) 100Ti Tz xTz
=-50).
30 , 89 , , 92 147,
17 , ( .
6.1)
, . 6.2.
. 6.1. , in vitro
.
14
147
6.2.
47, 89 , (P
L
7
)
)
)
)
PG(50%)
LC50): – 1
;
; –
147
;
– 89
89
228
GI50, PG
– 147
G(0%)
;
)
)
)
)
T
;
; – 89
TGI, PG(-
; –
; – 89
-50%)
; –
147
229
, 147
(GI50, TGI LC50
10-6 – 10-5 / )
U251 SNB-75 ( . 6.2 ),
– UO-31, ACHN A498 ( . 6.2 ) –
OVCAR3 ( . 6.2 ). 147
( . 6.2 ).
.
4,6- -(2- )-2-( -2- )-1,2,5,6- -
89
LOX IMVI ( . 6.2 ),
RXF 393 ( . 6.2 ). 4,6- -(2- )-2-(2- )-1,2,5,6-
89
RXF 393 ( . 6.2 ),
RPMI-8226 ( . 6.2 ).
30 92
.
,
1,2,5,6-
,
.
, ,
, ,
.
230
6.2. 5
.
(IC90) 90%
Mycobacterium tuberculosis H37Rv (ATCC 27294) [555],
100 / 0,19 / .
, 10
/ , (CC50),
Cell Titer Glo Luminescent Cell (CTG) ( VERO).
, (SI),
50 IC90 10,
,
. . in vivo.
48 , , 89 , , , , 92 .
89 .
, ( . 6.1) ,
, . . IC50 IC90.
CC50,
SI (0.334 - 0.852).
,
1,2,5,6-
,
.
5 TAACF (The Tuberculosis Antimicrobial Acquisition and Coordinating Facility), National Institute of Health (USA)
231
6.1 in vitro 48 , , 89 , , , , , 92
Mycobacterium tuberculosis ( H37Rv) IC50
(μg/mL) IC90
(μg/mL) 50
(μg/mL) SI
48 4.516 7.101 4.226 0.595
48 3.721 6.906 5.890 0.852
89 3.669 4.699 2.827 0.601
89
98%
6.25 μg/mL*
89 1.812 2.473 0.872 0.352
89 7.153 9.586 5.858 0.611 N
NHHO
S
89 6.236 9.989 3.344 0.334
89 1.018 3.248 1.71 0.526
92 5.454 7.605 3.399 0.446
232
6.3. 6
27 , 41
43 ( . 6.3) [556, 557].
. 6.3. ,
0,1% 0,2 ( = 10,65).
. ( 0,1%
0,2 ) ( 0,1% 0,2
)
.
25 125 / .
35-36 ° . L-
.
, :
% = [1-( / )]*100%
–
( ) ( )
, .
6
( . , ).
233
6.2
, / , %
48 125 0.204±0.008 10.2 25 0.225±0.007 0
54 125 0.338±0.008 -48.89
25 0.217±0.009 4.4
55 125 0.304±0.010 -33.9
25 0.223±0.005 0
L- 125 0.011±0.001 95.0
25 0.102±0.011 45.0
– 0.227±0.009 –
( . 6.2) , 54 , 55
,
.
5.2. 7
in vivo 148
149,
150.
« »
2.0-2.5 .
35 / .
100 /
(
)
« – ».
150
( . 6.4) 5 / . 2, 4,
6 8 .
7 « . . .
»
234
. 6.4. (148 149) (150)
148 ( )
,
( . 6.3). 149 2 4
, 6
. ,
149 - .
18-20
. . [558]. 50, -
. . [559] 148 149 1530 125.0
1647 83.6 / . 50 2700 220.0
/ . . . [560]
.
,
.
,
,
.
6.3
1
48, 1
49 (X
S),
n=4
-
, /
, /
,
2 4
6 8
, /
%
, /
%
, /
%
, /
%
148
100
15.9
0.8
12.9
0.72)
18
.71.
7 1)
2)
11.3
0.72)
28
.92.
81).2
) 11
.50.
52)
27.4
1.81)
.2)
12.2
1.02)
23
.72.
81)
149
100
13.1
1.4
12.5
1.62)
4.
82.
02)
11.4
1.32)
12
.70.
92)
10.8
0.92)
17
.01.
61).2
) 11
.61.
02)
10.9
1.52)
-
12.6
0.7
12.1
0.92)
4.
41.
92)
11.4
0.82)
10
.11.
72)
11.9
0.82)
5.
62.
32)
11.5
0.92)
9.
62.
32)
- 5
13.7
0.7
7.8
0.6
43.4
2.2
7.3
0.3
46.3
1.6
8.1
0.1
40.7
3.3
8.6
0.4
36.5
6.2
____
____
____
__
1)
(P<0
,1).
2)
,
(P
<0,1
). 3)
n –
234
236
,
,
,
« »
.
:
1.
,
- -
:
1.1. :
- -
;
- -
;
-
, ;
1.2. - :
-
;
-
;
237
-
;
-
,
;
2. 3- -1,2,4- 4- 5-
,
5- [1,5-a]
7- [1,5-a] . 3- -
1,2,4-
,
3- -2- .
3.
3- -5-
1,3-
:
-
[3,4-b] ;
– [5,1-b] ;
( - ) 150 °
,
- [4,3-c]-
.
- ,
238
.
4. 3- 5-
:
25 °
,
[3,4-b] -5,5’- ,
[4’,3’:5,6] -
[2,3-d] .
5. 5- -N- -4-
1,3-
[5,1-b] ,
[1,5-a] .
6.
5- 3-
-2- , [1,5-a] -5-
.
7. -
2,(2),4,6- ( ) 1,2,5,6- . -
20-30
,
,
.
8.
6- ,
1,3-
239
,
5- [3,4-b] ,
.
9. -
3- -
1,2,4- , 3- -5- 5- -N- -4-
1- -2- .
10. ,
, ,
,
,
.
11.
, ,
,
.
240
241
1.
EmrysTM Creator EXP, EmrysTM Synthesizer EmrysTM Initiator ( Biotage
AB, )
2.45 .
"high
absorbance level".
( "fixed hold times").
.
Discover ( CEM, )
.
( , ),
44.2 .
2.
5-( )-2H-
1,2,4- -3- 5 , 37 [3], 3- -5- 13 [561], 5- -
N- -1H- -4- 18 [562],
22 [563, 564], 5- -1- -3- 29 [3, 565, 97],
25, 27, 43, 46, 56, 66 [566, 567, 568], , - 76, 87 [3, 569],
65 [570], 69, 70 [571, 572, 573], -
108, 127 [574] VIII [575].
242
2- -4- -3- (3 ). (2.5 ,
63 ) 20 50%
20 3.1
(30 ) 2.6 (2 , 30 )
20 . 6 .
- , ,
.
pH 2.5.
, .
2.1 (45%), 62-63 ° .
3 - .
3,5- -1-(4- )-1,2,4- (10). 4-
(50 , 0.35 ) 29 (0.35 )
200 6 . 4
.
. .
43 (60%). 198-200 ° .
4- -1,2- (126). 5.0 (23 ) 2- -4-
50.0 (194 ) Na2S 10H2O 70
100 5 .
,
– (2:1), – (1:1).
3.3 (76,7%), 63-64 ° .
(116 ). 0.169 (7.0
) , .
243
. .
10 . ,
1.5 (6.4 ) 4-
15 . ,
. 1.5- 2
0 ° .
2.15 (19.2 ) ,
1 ,
. 200 16%- HCl 2
. ,
. 0.79 (62 %) 116 .
.
3.
7- -4,7- [1,5-a] -5-
(6 ). 1 (6 ) 3 , 0.5
(6 ) 5- 4 0,5
( 5 ), .
10 5 .
, .
6 - 7 -
8 - , .
7- -4,7- [1,5-a] -5-
(7 ). 3- -1,2,4- 5 (0.17 , 2 ),
2 (0.212 , 0.2 , 2 ) 1
(0.176 , 0.14 , 2 ) 3
4 . 10 .
244
,
.
6 - , , , 7 - .
7- -5-(4- )-4,5,6,7- [1,2,4]-
[1,5-a] -7- (9 ). 0.2 (2.3
) 3- -1,2,4- 5 , 0.24 (2.3 ) 2 0.2
(2.3 ) 1 4
120 25 ° .
3 ,
.
9 .
3-(5- -1-(4- )-1 -1,2,4- -3- )-5-(4-
) -2(5 )- . (11 ).
( I). 3,5- -1-(4-
)-1,2,4- 10 (0.42 , 2 ), 4- 2 (0.37
, 2 ) 1 (0.18 , 0.14 , 2 )
0.3 ( 10 ),
15 EtOH.
, .
( II).
10 (2 ) 3
(2 ) 0.3 .
11 , .
3- -4- -1H- [3,4-b] -6-
(14 ). 5- -3- 13 (1.1 )
3 (1.1 ) 1
1 . 5
245
.
.
.
14 , 16 - 14 , , 15 , .
. 15 16
.
1,4- -3- -1H- [3,4-b] -6- -
(14 ). 5- -3- -1- 13 (1.1 )
3 (1.1 ) 30 0.7
. 5 .
,
.
14 .
1,4- -3- -4,7- -1H- [3,4-b] -6-
(15 ). 5- -3- -1- 13
(1.1 ) 3 (1.1 ) 30
3 .
.
15 .
2,7- -4,7- [1,5-a] -5-
(16 ). 5- -3- 13 0.17 (1.1 )
3 0.19 (1.1 ) 3
60 25 ° .
,
.
16 - .
246
6- -3- -1H- [3,4-b] -4-
(17 )
. 3- -5- 13 (0.19 ,
2 ), 1 (0.18 , 0.14 , 2 )
2 (0.22 , 0.21 , 2 ) 30 3
.
, , ,
.
. 3- -5- 13
(0.19 , 2 ), 1 (0.18 , 0.14 , 2 )
2 (0.22 , 0.21 , 2 ), 2 2
5 , ,
. 10
150 ° .
, .
17 - , - .
1,6- -3- -1H- [3,4-b] -4-
(17 ). 0.19 (1.1 ) 5- -3- -1-
13 , 0.1 (0.08 , 1.1 ) 1 0.12 (0.11 ,
1.1 ) 2 30 0.5 .
5
. ,
.
.
17 - .
7-(4- )-3-( )-4,7- - [1,5-
a] -5- (19 ).
247
( I). 5- -N- -1 -
-4- 18 (0.2 , 1 ), 4- 2
(0.14 , 0.13 , 1 ) 1 (0.09 , 0.07 , 1
) 3 2 .
,
.
.
( II).
(1 ) 5- -N- -1 - -4-
18 4- 3
5
10 .
, .
( II).
0.2 (1 ) 5- -N- -1 -
-4- 18 0.2 (1 ) 4- -
3 10 4 ,
,
2 160 ° .
,
.
19 - .
5-(5-(4- )-2- -2,5- -3- )-N-(4-
)-1H- -4- (20 ). 5- -N-(4-
)-1H- -4- 18 (0.25 , 1 ) 4-
3 (0.21 , 1 )
30 5 .
.
20 , , .
248
7- -5,6- -4,5,6,7- -[1,2,4] -[1,5-
a] -7- (23 )
. 0.2 (2.3 ) 3- -1,2,4-
5 , 0.24 (2.3 ) 2 0.39 (2.3 )
22 4
30 .
, .
. 0.2 (2.3 ) 3- -1,2,4-
5 , 0.24 (2.3 ) 2 0.39 (2.3 )
22 4
5 . .
.
. 0.2 (2.3 ) 3- -1,2,4-
5 , 0.24 (2.3 ) 2 0.39 (2.3 )
22 4 5
2 120 ° .
, ..
23 - 25 - ( 3- -1,2,4-
5- -N-(4- )-1H- -4-
18 ).
22
25 27.
3- -4,5- -1-(2H-1,2,4- -3- )-1H- -
2(5H)- (24 ).
. 0.2 (2.3 ) 3- -1,2,4-
5 0.24 (2.3 ) 2 0.39 (2.3 )
22 . 3
3 . 12 ,
249
6 . , ,
.
. 0.2 (2.3 ) (2.3 ) 3-
-1,2,4- 5 , 0.24 (2.3 ) 2 0.39 (2.3
) 22 3 5
, ,
20 170 ° .
5 , ,
.
24 - , 30 - 26 - .
22 25 27.
23 ( ).
23 0.2 (0.6 ) 3 5
, ,
20 170 ° .
, .
9 25.
4-(4- )-3- -5- -1H- [3,4-b] -
6- (29 ). 0.2 (2 ) 13 , 0.28
(0.25 , 2 ) 4- 2 0.34 (2 )
22 3
3 . 3
.
.
29 - .
6- -7-(4- )-4,7- [1,5-a]
-5- (31 ). 6 (0.3 , 1 )
250
0.06 5 , 10
.
. .
.
7-(4- ) [1,5-a] -5-
(32 ).
. 31 (0.2 , 0.5 ) 0.06 (1.5
) 5 .
60 ° 2 .
.
.
.
. 7 (0.2 , 0.7 ) 0.5
0.3 M , 0.11 (2 ) ,
5 , 5 .
. .
.
5- -2- -N,7- -4,7- -1,2,4- - [1,5-
a] -6- (38 ).
. 3- -5- -1,2,4- 37
(0.13 , 1 ), 34 (0.18 , 1 )
2 (0.11 , 1 ) 0.05
5 . 15
, ,
, .
. 3- -5- -1,2,4- 37
(0.13 , 1 ), 34 (0.18 , 1 )
2 (0.11 , 1 ) 3.0 5 ,
251
,
(120 ° , 5
).
.
38 - .
2-( )-7- -7- -5-(4- )-N-(2-
)-4,5,6,7- [1,2,4] [1,5-a] -6-
(39 ). 3- -5- -1,2,4- 37 (0.20 , 1
), 4- 2 (0.13 , 1 )
34 (0.18 , 1 )
25 ° 1 . ,
.
20 - , , .
39 38 . 39
(0.530 , 1 ) 1 3 ,
10 . 38
, .
4,5,6,7-
[1,2,4] [1,5-a] -6- 39,
4,5,6,7- [1,5-a] -3,6- 41.
5-(4- -3- )-7- -7- -N- -4,5,6,7-
[1,5-a] -3,6- (41 ).
5- -1 - -4- 18 (0.126 , 1 ), 4-
-3- 2 (0.170 , 1 ),
34 (0.180 , 1 ) 10
25 ° 1 .
, .
252
41 - .
34 43.
5- -7-(4- )-N- -4,7- -[1,5-
a] -3,6- (42 ). 5- -1 - -4-
18 (0.126 , 1 ), 4- 2 (0.120 , 1
) 34 (0.180 , 1 ) 0.1
10 , 20 .
,
.
42 - .
34 43.
7-(4- )-2,5- -N- -4,7- - [1,5-
a] -6- (44 ).
5- -3- -1 - 13 (0.097 , 1 ), 4-
2 (0.131 , 1 )
34 (0.180 , 1 ) 1 20 .
10 ,
, .
44 - .
4-(4- -3- )-3,6- -N- -4,7- - -
1 - [3,4-b] -5- (45 ).
5- -3- -1 - 13 (0.097 , 1 ), 4- -
3- 2 (0.166 , 1 )
34 (0.180 , 1 ) 1 20 .
253
10 ,
, .
45 - .
7,7- -4-(4- )-3- -1,4,6,7,8,9- - -5H-
[3,4-b] -5- (48 ). 10 0.21
(1.3 ) 5- -3- 13 , 0.18 (1.3 ) 5,5-
-1,3- 47 , 0.16 (1.3 ) 4-
2 3.0 0.1 . ,
,
15 150 ° .
4.0 - (1:1) 50-60 ° ,
, 10 - (1:1)
.
48 - .
6,6- -9-(4- )-2- -5,6,7,9- -
[5,1-b] -8(4H)- (49 ).
. 5 0.21 (1,3
) 5- -3- 13 , 0.18 (1.3 ) 5,5-
-1,3- 47 , 0.16 (1.3 ) 4-
2 2 .
(25 ° , 30 ).
5 - (1:1).
,
, .
. 20 ,
, 10 , 3- -5- 13 (1.39
, 8.74 ) 5,5- -1,3- 47 (1.23 , 8.74 )
254
.
(0,22 , 190 , 1.75
) 1 ,
4- 2 (0,51 , 525 , 4.37 ).
,
30
170 °C.
, 300
(2:1), 160 NaOH (pH 8-9).
1 ,
(2:1), 0 °C.
2- - (2:1).
49 - .
5a- -3- ( )-4- -4,5,5a,6,7,8- -
[4,3-c] -9- (29).
. 0.21 (1.3 ) 5- -3-
13 , 0.18 (1.3 ) 5,5- -1,3- 47
(1.3 ) 2 ,
3 0.17 (2.6 ) ,
15 150 ° .
, 4 - (1:1)
50-60 ° ,
, 10 - (1:1) .
. 0.36 (2.6 ) 5,5-
-1,3- 47 , 2 (1.3
) 0.17 (2.6 ) 5 2
,
255
2 100 ° .
1 0,21 (1,3 ) 5- -3-
13
15 150 ° .
, 4 - (1:1)
50-60 ° .
, 10 - (1:1) .
. 0.21 (1.3 ) 5- -3-
13 , 2 (1.3 ) 0.08
(1.3 ) 2 ,
10 150 ° . 1
0.18 (1.3 ) 5,5- -
1,3- 47 15
150 ° .
, 4 - (1:1)
50-60 ° . ,
10 - (1:1) .
50 - .
6,6- -N- -8- -9-(4- )-4,5,6,7,8,9-
[5,1-b] -3- (54 ).
. 0.3 (1.5 ) 5- -N- -1 -
-4- 18 , 0.18 (1.5 ) 4- 2
0.21 (1.5 ) 5,5- -1,3- 47 , 2
15 . 50-60 °
4 - (1:1). ,
, .
. 0.3 (1.5 ) 5- -N- -1 -
-4- 18 , 0.18 (1.5 ) 4- 2
256
0.21 (1.5 ) 5,5- -1,3- 47
45 25 ° ,
- (1:1)
(~ 60 - 70 °C).
.
54 - .
5,5- -1,3- 47
56 .
8,8- -N- -5-(4- )-6-o o-4,5,6,7,8,9-
[1,5-a] -3- (55 ). 0.2 (1
) 5- -N- -1 - -4- 18 , 0.14 (1 )
4- 2 0.28 (2 ) 5,5- -1,3-
47 , 1,5
45 25 ° . 4
- (1:1), , ,
.
55 - .
5,5- -1,3- 47
56 .
5-[9-(4- )-3,3,6,6- -1,8- -2,3,4,5,6,
7,8,9- -10(1 )- ]-N-(4- )-1 - -4- -
(57 ). 0.32 (1.5 ) 5- -N-(4- )-1 -
-4- 18 , 0.21 (1.5 ) 4- 2
0.42 (3 ) 5,5- -1,3- 47 , 2
60
. 50-60 ° 4 -
(1:1). , 57 54 ,
257
.
57
- (2:3)
57 .
3,3,6,6- -9,10- -1,2,3,4,5,6,7,8,9,10- -
-1,8- (60 ). 0.42 (3 ) 5,5-
-1,3- 47 , 0.16 (1.5 ) 2
0.14 (3 ) 59 1 2
.
3 , ,
80% .
5 - .
3- -4-(4- )-1- -1 - [4',3':5,6] -
[2,3-d] -5,7(6 ,8 )- (62 ).
. 5- -3- -1- 13
(0.173 , 1 ), 61 (0.128 , 1 ) 4-
2 (0.134 , 1 ) 30 2
. 20 ,
, ..
. 5- -3- -1- 13
(0.173 , 1 ), 61 (0.128 , 1 ), 4-
2 (0.134 , 1 ) 2 ,
,
(190 ° , 3 ).
25 ° 20 .
, .
62 - .
258
4-(4- )-3- -4,9- -1 - [4',3':5,6]-
[2,3-d] -5,7(6 ,8 )- (63 ). 5- -3-
13 (0.082 , 1 ), 61 (0.128 , 1
) 4- 2 (0.134 , 1 ) 2
30 . 20 .
, .
63 - .
4-(4- )-3- -1 - [4',3':5,6] [2,3-d]-
-5,7(6 ,8 )- (62 ). 63 (0.645 , 2 )
4
0.4 , 2
. .
62 - .
4,6- -1,4,6,7- -2' - [ [3,4-b] - -
5,5'- (64).
. 5- -3- -1-
13 (0.173 , 1 ), 61 (0.128 , 1
), 4- 2 (0.305 , 2 ) 1
3
25 ° . , 15
, .
64 - .
.
65 (0.490 , 2 ) 66 (0.430 , 2 ) 1
30 , , 15
. ,
.
64 .
259
. 61 (0.128
, 1 ), 4- 2 (0.150 , 1 ) 66
(0.215 , 1 ) 1
3 25 ° , 15
. ,
.
64 - .
. 5- -3- -1-
13 (0.173 , 1 ), 4- 2 (0.150 , 1
) 65 (0.262 , 1 )
1 3 ,
15 . ,
.
64 - .
8,8- -5-(4- )-2- -2,3,5,8,9- -
[4,5-b] -4,6- (68 ). 10
0.16 (1.3 ) 6- 67 , 0.18 (1.3 ) 5,5-
-1,3- 47 , 0.16 (1.3 ) 4-
2 1 .
1 , 0.1 ,
,
10
150 ° . , 10
.
68 - .
5,7- [2,3-d] -2,(4)-( ) (77).
. 5,7- [2,3-d] -2,4- (77 ).
1.27 (10 ) 6- 67 , 2.08 (10 ) 76
260
1.01 (10 ) 5 3-
. 10 .
,
, .
77 - .
. 5-(4- )-7-(4- ) [2,3-d] -
-2,4- (77 ). 1.27 (10 ) 6- 67 , 2.56 , (10
) 76 1.76 (10 ) N-
5 3- . 10
.
, .
77 - .
5-(4- )-7-(4- )-5,8- [2,3-d]-
-2,4- (78 ). 1.27 (10 ) 6- 67
2.56 (10 ) 76 10
3- .
, .
78 - 79 , .
4-(2- )-6-(4- )-1,2,5,6- -
(89 ). . 87 (0.25 , 1 )
(0.03 , 1 ) 2 , ,
90
25 ° . .
89 - , - .
4-(2- )-6-(2,5- )-2-(4- - )-
1,2,5,6 (89 ). .
87 (0.284 , 1 ), 2 (0.136 , 1 ),
261
(64 , 4 ) S-
90 25 ° .
.
89 , .
9- -4-(2- )-2- -1,5,9- -
[5.5] -1- (92 ). 87 (0.22 , 1 ) -
91 (0.19 , 1 ) 2
90 25 ° .
.
92 - .
89 3-
. 89 (0.2 , 0.713 ) 3-
2 (0.11 , 0.713 )
(0.05 , 0.713 ) 20 20
25 ° . 89 ,
.
6-(2,5- )-4-(2- )-2-(4- -
) (100 ). 89 (0.420 ,
1 ) 0 °
(0.06 , 3 ),
3
25 ° . .
100 , , 101(102) , .
3,3- -5-(2- )-1-(4- )-3,5a- -1H-
[1,2-c] (111). 0.926 (2.0 ) 2,3- -
1-(2- )-3-(4- )-1- 108 10
262
.
0.34 (0.29 , 5 ) ,
2 . ,
.
.
112, 114, 115 , , 118, 120, 133, 145.
2-(2- )-1-(4- )-1,1a- [1,2-a]-
(113). 0.926 (2.0 ) 2,3- -1-(2- )-3-(4-
)-1- 108, 0.324 (3.0 ) 1,2- 110
1.11 (0.808 , 8.0 ) 10
( 10 ), 2
, ,
– (1:1),
.
124, 128 - , 131 - , 135.
6-(4- )-1-(4- )-1,3,4,6a- - [1,2-
a]- (122). 4.92 (10 ) 2,3- -1-(4- )-3-(4-
)-1- , 1.0 (0.9 , 15 ) 4.17
(0.606 , 30 ) 70
( 15 ), 20
, ,
– (1:1).
134 136.
3,3- -5-(4- )-1-(4- )-3,5a- -1H-
[1,2-c] (117 ).
. 1.0 (2.59 ) 115 ,
0.379 (3.1 ) 116 , 30 , 15
263
3 -
.
56 (0.069 ) PdCl2dppf·CH2Cl2,
,
0.87 (10.36 ) NaHCO3 15 .
3, 5,
10, 30, 70 140 .
.
, ,
0.3 .
5
.
, (2×15 ),
(50 ),
Na2SO4, (~ 20 3),
.
117 , , 119, 121, 123.
1-(4- )-2-(4- )-1,1a- -[1,2-a]-
(129 ). . 1.09 (2.59 )
128 , 0.379 (3.1 ) 116 , 0.30
, 30 , 15 3 -
. 56 (0.069
) PdCl2dppf·CH2Cl2, ,
0.87 (10.36 )
NaHCO3 15 .
20
. ,
(2×15 ),
264
(50 ), Na2SO4, (~20 3)
.
. 0.92 (85 %) 23.
. . 147-148 ° .
129 - . 129
, 128 1.28
, 25 .
8-(4- )-6-(4- )-1- -3,7,8,9- -
4H- [3',4':3,4] [1,2-a] -7,9- (139). 146.5
(0.5 ) 136 109 (0.5 ) N-(4- )
137 3 3 .
139.
7,8- -1,2- (4- )-4- -1,2- -3aH-[1.3]-
[3,2-a] (141 ). 1.0 (2.58 )
131 0.39 (2.6 ) 4- 2 30 30
,
2 . ,
.
2/3 .
7(8)- -1,2- (4- )-4- -1,2- -3aH-[1.3]-
[3,2-a] 71 ( A ). 2.5 (7 )
131 1,1 (7.3 ) 4- 2 25
45 2 .
.
265
7(8)- -1,2- (4- )-4-(4- )-1,2- -
3aH-[1.3]- [3,2-a] 72 ( A ). 550 (1.27
) 131 196 (1.3 ) 4- 2 15
30 ,
2 .
.
.
. 1,2- (4- )-4- -1,2-
-3aH-[1.3] [3,2-a]- (141 ). 0.171 (0.5
) 131 0.076 (0.6 ) 4- 2 4
40 , 3 , ,
.
141 , 142 - .
. 8-(4- )-10-(4- )-6-
-6b,7,8,9,9a,10- -6aH- [3',4':3,4] [1,2-a]-
-7,9- (142 ). 0.171 (0.5 ) 131
0.096 (0.5 ) N-(4- ) 137 15
40 25 ° .
,
.
. 1,2- (4- )-4-(4-
)-1,2- -3aH-[1.3] [3,2-a] (141 ).
36.9 (0.1 ) 131 18.1 (0,12 ) 4-
2 2
-120
90 .
.
141 , , 142 - .
266
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