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Synthesis of 5 H ‐Tetrazolo[1,5‐ d ] [1,4]benzodiazepin‐6(7 H )ones
Author(s) -
Peet Norton P.,
Sunder Shyam
Publication year - 1977
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.5570140406
Subject(s) - chemistry , ring (chemistry) , tricyclic , bromide , transformation (genetics) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , gene
Syntheses of 5 H ‐tetrazolo [1,5‐ d ] [1,4 ]benzodiazepin‐6(7 H )ones 2a‐d from 5‐( o ‐aminophenyl)‐tetrazoles 1a‐d and bromoacetyl bromide are described. Compounds 2a‐d are representatives of a novel tricyclic ring system. Several alternate methods for the synthesis of 2a‐d were attempted without success. Spectral evidence for structural assignments 2a‐d is presented. Chemical evidence for these assignments includes the transformation of 2a to 6‐(2,2‐dimethylhydrazino)‐5 H ‐tetrazolo[1,5‐ d ] [1,4]benzodiazepine ( 19 ) via the thione analog of 2a ( 18 ).