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Synthesis of novel imidazo[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepines and pyrimido[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepines
Author(s) -
Duceppe JeanSimon,
Gauthier Jean
Publication year - 1985
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.5570220214
Subject(s) - chemistry , formylation , benzodiazepine , imidazole , ring (chemistry) , pyrrole , medicinal chemistry , stereochemistry , amidine , benzazepines , organic chemistry , catalysis , receptor , biochemistry
Several 1 1‐amino‐5 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepines have been used as starting material to prepare a number of derivatives of 9 H ‐imidazo[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepines and 10 H ‐pyrimido[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepines. The imidazole nucleus was built by reaction of amidines with ethyl bromopyruvate or aminoacetaldehyde dimethylacetal. Several derivatives of imidazo[1,2‐ a ]pyrrolo[2,1‐ c ][1,4]benzodiazepine have been prepared by formylation of the pyrrole ring followed by formation of thioamides. Condensation of 11‐amino‐5 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepines with diethyl ethoxymethylenemalonate afforded intermediate diesters which were transformed into the corresponding 10 H ‐pyrimido[1,2‐ a ]pyrrolo[2,1‐ c ]‐benzodiazepines.