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Polycondensed nitrogen heterocycles. VII. 5,6‐Dihydro‐7‐h‐pyrrolo[1,2‐ D ]‐[1,4] benzodiazepin‐6‐ones. A novel series of annelatcd 1,4‐benzodiazepines
Author(s) -
Aiello Enrico,
Dattolo Gaetano,
Cirrincione Girolarno,
Plescia Salvalor E.,
Daidone Giuseppe
Publication year - 1979
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.5570160201
Subject(s) - chemistry , triethylamine , bromide , catalysis , nitrogen , medicinal chemistry , bicyclic molecule , ring (chemistry) , organic chemistry , stereochemistry
Abstract The synthesis of a novel class of annelated 1,4‐benzodiazepinen, the 2‐R‐3 methyl‐5,6‐dihydro‐7 H ‐pyrrolo[1,2‐ d ][1,4]benzodiazepin‐6‐ones (Ve‐e), is described. The reaction of 2‐(o‐aminophenyl)‐3‐R‐5‐methylpyrroles(IIIa,b) with bromoacetyl bromide in the presence of triethylamine produced the title compounds. An alternative synthetic route was achieved by means of the reactions of 1a,b with the appropriated α‐aminoacids. The catalytic reduction of IVe‐e over 10% palladium on charcoal led in good to excellent yields directly to the formation of pyrrolo[1,2‐ d ]‐[1,4]benzodiazepines (Ve‐e).