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Paper | Regular issue | Vol 85, No. 7, 2012, pp.1671-1681
Published online, 5th June, 2012
DOI: 10.3987/COM-12-12501
Reaction of 1-Ethoxyisoindole with Maleimide and Its Derivatives

Igor V. Levkov, Stephanie Cassel, Zoia V. Voitenko,* Gennady V. Palamarchuk, Oleg V. Shishkin, Svetlana V. Shishkina, Armand Lattes, and Isabelle Rico-Lattes

*Department of Organic Chemistry, Kiev National Taras Shevchenko University, 64 Str Volodymyrs’ka, 01033 Kiev, Ukraine

Abstract

We have reported1 the possibility of conducting the Diels-Alder [4+2]-cycloaddition reaction with isoindoles that exist predominantly in the isoindoline form, due to the Curtin-Hammet principle. Pursuing our research, we used 1-ethoxyisoindole as the most evident analog of 1-aminoisoindole. This compound is a typical simple isoindole existing chiefly as the isoindoline tautomer. We have studied the reactions of 1-ethoxyisoindoles with maleimide and its derivatives as active dienophiles. In addition, this paper describes the synthesis of a novel compound – tri-(2-methoxycarbonyl)benzylamine.