Premium
Research on nitrogen containing heterocyclic compounds. XIX : Synthesis of 8 H ‐imidazo[2,1‐ c ]‐ s ‐triazolo[4,3‐ a ]‐[1,4]benzodiazepine and its 1‐derivatives
Author(s) -
Stefancich Giorgio,
Silvestri Romano,
Artico Marino
Publication year - 1993
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.5570300243
Subject(s) - chemistry , sodium ethoxide , imidazole , medicinal chemistry , derivative (finance) , sodium iodide , potassium , iodide , catalysis , lactam , chloride , iodine , stereochemistry , organic chemistry , ethanol , financial economics , economics
Abstract Reaction of 2‐nitrobenzyl iodide with 1 H ‐imidazole, in the presence of potassium tert ‐butoxide and 18‐crown‐6, gave 1‐(2‐nitrobenzyl)‐1 H ‐imidazole. Trichloroacetylation of this compound furnished trichloroacet‐ylimidazole 8 , which on treatment with sodium ethoxide was transformed into the corresponding ethoxycarbonyl derivative 9 . Catalytic reduction of the nitro group to the amino group yielded 10 , which was then cyclized to 10,11‐dihydro‐11‐oxo‐5 H ‐imidazo[2,1‐ c ][1,4]benzodiazepine 11. Treatment of this lactam with di‐4‐morpholinylphosphinic chloride followed by reaction of the intermediate 12 with formylhydrazine gave the title compound or its 1‐derivatives when acetylhydrazine or isonicotinoylhydrazine were used instead of formylhydrazine.