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Research on nitrogen containing heterocyclic compounds. XVII . Synthesis of 8 H ‐diimidazo[1,5‐ a :2′,1′‐ c ][1,4]benzodiazepine, a novel tetracyclic ring of pharmaceutical interest
Author(s) -
Stefancich Giorgio,
Artico Marino,
Silvestri Romano
Publication year - 1992
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.5570290233
Subject(s) - chemistry , nitromethane , benzodiazepine , derivative (finance) , ring (chemistry) , stereochemistry , formaldehyde , medicinal chemistry , organic chemistry , biochemistry , receptor , financial economics , economics
The synthesis of 8 H ‐diimidazo[1,5‐ a :2′,1′‐ c ][1,4]benzodiazepine 6 , a novel nitrogen‐containing tetracyclic ring, is reported starting from 5 H ‐imidazo[2,1‐ c ][1,4]benzodiazepine 7. Reaction of this compound with nitromethane and subsequent reduction of the obtained nitromethyl derivative 8 afforded 11‐aminomethyl‐10,11‐dihydro‐5 H ‐imidazo[2,1‐ c ][1,4]benzodiazepine 9. Treatment of the latter compound with formaldehyde led to 1,2,3,3a‐tetrahydro‐8 H ‐diimidazo[1,5‐ a :2′,1′‐ c ][1,4]benzodiazepine 10 , which was then oxidized to the title compound.