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On the reaction of 3‐nitro‐1,2‐phenylenediamine with ethyl acetoacetate. Condensed dihydrodiazepinones
Author(s) -
Puodžiūnaitė Benedikta,
Kosychova Lidija,
Stumbrevičiūtė Zita,
Jančienė Regina,
Talaikytė Zita
Publication year - 1999
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.5570360430
Subject(s) - chemistry , ethyl acetoacetate , nitro , derivative (finance) , condensation , medicinal chemistry , boiling , organic chemistry , catalysis , alkyl , physics , financial economics , economics , thermodynamics
Condensation of 3‐nitro‐1,2‐phenylenediamine with ethyl acetoacetate in boiling xylene gave two isomeric 2,3‐dihydro‐4‐methyl‐9‐nitro‐ and 2,5‐dihydro‐4‐methyl‐6‐nitro‐1 H ‐1,5‐benzodiazepin‐2‐ones, the 9‐nitro derivative thermal rearrangement product N ‐isopropenyl‐4‐nitrobenzimidazolone and a non cyclic acetoacetamide derivative. At room temperature these reactants afforded 2,3‐dihydro‐2‐ethoxycarbonyl‐methyl‐2‐methyl‐4‐nitrobenzimidazole.