Premium
Diazepines II. A new synthesis of 4 h ‐pyrrolo[ 1,2‐α] ‐[1,41] benzodiazepine
Author(s) -
Kayama Yasutaka,
Hara Takeshi,
Itoh Kazuhiko,
Sunami Tamiko
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.5570140137
Subject(s) - chemistry , hydrazine (antidepressant) , benzodiazepine , benzophenone , hydrate , condensation , d 1 , medicinal chemistry , stereochemistry , organic chemistry , chromatography , receptor , biochemistry , physics , thermodynamics
Abstract A convenient synthesis of a 4 H ‐pyrroIo[1,2‐α][1,4 ]benzodiazepine is described. 2,5‐Di‐methoxy‐2‐melhyl‐5‐phthalimidomethyltetrahydrofuran ( 3 ) was prepared starting from 2‐methyl‐5‐phthalimidomelhylfuran ( 1 ). The condensation of 2‐amino‐5‐chlorobenzophcnone with 3 to give 5‐chloro‐2‐(2‐methyl‐5‐phthalimidomethylpyrro]‐1‐yl)benzophenone ( 4 ), the treatment of which with hydrazine hydrate afforded 8‐chloro‐1‐methyl‐4 H ‐pyrrolo[1,2‐α] [1,4]benzodiazepine ( 5 ).