CYCLOADDITION OF FURFURYLAMINES TO MALEIC ANHYDRIDE AND ITS SUBSTITUTED DERIVATIVES

Abstract

The regio- and stereoselectivity of the [4+2] cycloaddition of maleic, citraconic, dichloromaleic, and dibromomaleic anhydrides to difurfuryl amines and secondary furfurylamines were studied. N-Furfuryl-, N-phenyl-, and N-benzylhexahydrooxoepoxyisoindole-7-carboxylic acids were synthesized. An approach was developed for obtaining hexahydroepoxyoxoisoindole-7-carboxylic acid unsubstituted at the nitrogen atom. Aromatization of the oxabicycloheptene fragment of the dihaloepoxyiso-indolonecarboxylic acids gave a series of 7-carboxy-2-R-isoindol-1-ones.

Authors: V. P. Zaytsev, N. M. Mikhailova, I. K. Airiyan, E. V. Galkina, V. D. Golubev, E. V. Nikitina, F. I. Zubkov, and A. V. Varlamov.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (3), pp 505-513

http://link.springer.com/article/10.1007/s10593-012-1023-1