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 structures (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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Additional resources for Chemistry of Heterocyclic Compounds: Azepines, Part 2, Volume 43

Example text

The synthesis of 43 (Y = NMe,) can also be achieved directly from 42 under Eschweiler-Clarke conditions (30). V. TABLE 4. 5,5,7-Systems 15 TETRAZALO[ 1 ,5-a]THIEN0[3,2-fl[1,4]DIAZEPINES Structure R! R2 X Yield (%) mp C'C) Refs. 42 42 42 43 (Y 43 (Y H H Me H Et Me Me Et CI CI CI CI 80 135- 136 122-123 149- 150 170- 17 I" 29 29 29 30 Me Me CI 189- 190 30 = NMeZ) = NMe,) 77 77 "Oxalate. 2. [1,2,4]0xadiazolo[4,3-a]thieno[3,2-Jl[l,4]diazepines [ 1,2,4]0xadiazolo[4,3-~]thieno[3,2--[ 1,4]diazepines were prepared as shown in Eq.

TABLE 14. IMIDAZO[I ,2-a]THIEN0[3,2-f][ I ,4]DIAZEPINES ~~ R, R2 X H H 0-CI H H H H H H H H H Me Et H Me Et Et Et Et Et Et Me H H “Refs. 29 and 30. 0-c1 0-CI o-Br 0-F P-F o-Me0 p-Me0 0-CI Yield (%) 80 78 mp Salt 124- I27 243-245 96-98 156- I57 252-253 180-1 82 237-238 95-96 116-1 17 215-216 173-175 131-132 HCI ~~ 2HCI $ N 0x1 Et Et Et H H H “Refs. 30 and 36. N 0-CI Et H 0-c1 0-CI 0-c1 0-c1 0-c1 n WNMe f-7 73 NEl NHMe c1 CI NMe, CI NMe, C1 H H 0-CI 0-CI 0-F Et Et Et Et Et Me Et Et H H H H H Me H H Y X Rz K’ TABLE IS.

NO Me Et 107 110, mp 181-184°C Ph i 108 ( I ) KOHlMeOH (2) HCI (3) HOAclNaNO, 109 12. 8) Several syntheses of the imidazo[1,2-althieno[3,2-fl[l,4ldiazepine system have appeared. Reaction of thienodiazepine-2-thione 112 (a key intermediate also used in the preparation of the corresponding tetrazolo and oxadiazolo tricyclic diazepines) with 2,2-diethoxyethylamine led to the diazepine 113, which was in equilibrium with its imino tautomer. Acid-catalyzed cyclization produced the tricyclic imidazole 114 as outlined in Eq.

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