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On the reaction of 3-nitro-1,2-phenylenediamine with ethyl acetoacetate. Condensed dihydrodiazepinones

✍ Scribed by Benedikta Puodžiūnaitė; Lidija Kosychova; Zita Stumbrevičiūtė; Regina Jančienė; Zita Talaikytė

Publisher: Journal of Heterocyclic Chemistry
Year: 1999
Tongue: English
Weight: 290 KB
Volume: 36
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570360430

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✦ Synopsis

Abstract

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.

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