Download Chemistry of Heterocyclic Compounds: Azepines, Part 2, by Andre; Renfroe, Burt; Watthey, Jeffrey W. H. Rosowsky PDF

By Andre; Renfroe, Burt; Watthey, Jeffrey W. H. Rosowsky

Dibenzodiazepines and different Tricyclic Diazepine platforms (J. Watthey & J. Stanton).

Monocyclic and Condensed Triazepines and Tetrazepine (N. Peet).Content:
Chapter I Dibenzodiazepines and different Tricyclic Diazepine platforms (pages 1–717): Jeffrey W. H. Watthey and James L. Stanton
Chapter II Monocyclic and Condensed Triazepines and Tetrazepines (pages 719–842): Norton P. Peet

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Other reactions of the basic tricyclic system (Eq. 16) included nitration of 73 to yield 74 (34) and photolysis of 75 to give the acetyl derivative 76 (38,45). In addition, the Hunsdiecker reaction with 77 led to bromothiophene r H N O,IH,SO, 73, 15, 77, R R R = = = H Et H02C 74 76 I I I 78 35 V. 5,5,7-Systerns derivative 78. Compounds synthesized by this process are included in Table 7 (46). Turning to reactions at the 1-position (Eq. 17), addition of bromine to 79 afforded 80. Displacement reactions on substrate 80 with methoxide, ethoxide, and methylmercaptide afforded the corresponding methoxy, ethoxy, and methylthio derivatives (81) (47).

Confinued) R, R2 R, X rnp ("C) Refs. 46 Me H COzEt CI 202 46 Me H C02H CI 300-303 46 N Me H Br CI 240-241 46 H CO2Et Br 204 46 H CO2H Br 295-297 46 H Br Br 190-191 46,47 H H H H H H H H H CO2Et C02H Br Br Br Br Br Br Br Br Br Br CI CI CI CI CI CI 212 288 204-206 211-213 214-216 210-21 1 198-200 158-160 144-146 38,46 38,46 37,46,47 37,47 47 37,47 47 47 47 H Br CI 140-142 47 b -0 -(=. Go 0 0 G -0 -0 -0 Me Me Me Me H Br Me0 MeS EtO 25 TABLE 7. (Continued) R, R* R7 X mp (“C) Refs. H Br CI 211-212 47 H Br CI 257-258 37,47 H Br CI 257-258 47 H CI CI 191 47 H Br CI 212-213 28,47 H Br CI 161-162 47 H Br CI 190-191 47 H Br c1 192-193 47 H H CI CI CI CI 170-172 160-162 47 47 H CI CI 188-189 47 H Et CI 128-129 47 H H H 178-180 47 H H H H H H H H Et Et H H CI CI CI CI H H 202-203 184-185 175-176 167-168 197-199 47 47 47 47 47 47 H Br c1 145-147 47 H Br CI 190-191 47 H Br CI 187-188 47 26 Oil TABLE 7.

The I-0x0 tricyclic ring system was also prepared from 60 by reaction with ethoxycarbonylhydrazine or by addition of hydrazine, followed by reaction with phosgene, to yield 62 (Fig. 4). These structures are included in Table 10. A I-thione compound (72)was also prepared from 60 by sequential addition of hydrazine and thiophosgene (40-43). 3'"' 67a 72, mp 236-237°C I 64 K,CO,IH,O R3- 65 Figure 4 23 61 TABLE 7. THIENO[~,~-~~[~,~,~]TRIAZOLO[~,~-U][~,~]DIAZEPINES R, R2 R, X mp ("C) Refs. 38 35,36,37,38 35 35,36,38 35,36,38 35,36,38 35,36,38 35,36,38 35 35,36,38 35,36,38 35,36,38 35,36,38 35,38 n W0 Et Ph H H Me H Me H H Me Me H H H H H H H H CI c1 CI CI CI CI c1 Et Et -(CH2)4-(CH2)4- Et Et H Me Me Me Et c1 c1 Et Et Et Et Et Et H Me F F Rr Br ~~ 24 TABLE 7.

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