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Synthesis of heterocyclic nitrogen derivatives from aryl-1,4-benzoquinones

✍ Scribed by Mamdouh A. Hassan; Ragab F. Fandy; Tark M. El-Amine

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 53 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380126

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✦ Synopsis

Abstract

Treatment of 2‐aryl‐3,6‐bis(arylamino)‐1,4‐benzoquinones 2a‐h with different acid chlorides, namely acetyl, phenylacetyl and chloroacetyl chloride yields 3a,7a‐dihydropyrrolo[2,3‐f]indole‐2,6‐dione 3, 5‐(N‐phenylacetylarylamino)‐3‐phenylindole‐2,6‐dione 4 and 3‐chloro‐5‐(N‐chloroacetylarylamino)indole‐2,6‐dione 5 respectively. Stirring 2‐aryl‐1,4‐benzoquinones (1) with ethylenediamine and/or o‐phenyl‐enediamine in methylene chloride gives pyrazino[2,3‐g]quinoxalines derivative 6 and/or tetrapentacene derivative 7 respectively. The products 5‐aryl‐ and 6‐aryl‐1/H‐indazole‐4,7‐diones 8 and 9 were obtained in the 1,3‐dipolar cycloaddition of diazomethane to (1).

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