Premium
Research on nitrogen containing heterocyclic compounds. XVIII . Synthesis of 9 H ‐pyrrolo[2,1‐ c ]‐ s ‐triazolo[4,3‐ a ][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.5570290457
Subject(s) - chemistry , ring (chemistry) , intramolecular force , stereochemistry , benzodiazepine , chloride , medicinal chemistry , benzazepines , nitrogen , bicyclic molecule , lactam , organic chemistry , biochemistry , receptor
Reaction of di‐4‐morpholinylphosphinic chloride on 5,10‐dihydro‐9 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepin‐11‐one 9 afforded 11‐(di‐4‐morpholinylphosphinyloxy)‐5 H ‐pyrrolo[2,1‐ c ][1,4]benzodiazepine 10 . Displacement of di‐4‐morpholinylphosphinyloxy group of 10 by formylhydrazine with concomitant intramolecular cyclization led directly to 9 H ‐pyrrolo[2,1‐ c ]‐ s ‐triazolo[4,3‐ a ][1,4]benzodiazepine 7, a novel nitrogen heterocyclic ring of pharmaceutical interest. A new procedure for the synthesis of 9 is also described.