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Tetracyclic benzodiazepines. 3. Synthesis of the 2,3‐dihydro‐1h‐quino[1,8‐ab][1,5]benzodiazepine ring system, and derivatives of potential biological interest
Author(s) -
Glamkowski Edward J.,
Chiang Yulin
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240337
Subject(s) - chemistry , ring (chemistry) , substituent , benzodiazepine , formamide , diazepine , stereochemistry , antipsychotic drug , antipsychotic , organic chemistry , receptor , biochemistry , schizophrenia (object oriented programming) , computer science , programming language
The synthesis of the 2,3‐dihydro‐1 H ‐quino[1,8‐ ab ][1,5]benzodiazepine ring system is described. The key step involves a Bischler‐Napieralski type cyclization of the formamide 3. This was achieved by refluxing in phosphorus oxychloride to effect a cyclodehydration to form the seven‐membered central ring. A subgroup of 1 H ‐quinobenzodiazepines bearing a pendant N ‐methylpiperazine substituent was synthesized by a similar cyclization of ureas of type 6. These derivatives 7 are structurally related to the antipsychotic drug clozapine.