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CYCLOADDITION OF FURFURYLAMINES TO MALEIC ANHYDRIDE AND ITS SUBSTITUTED DERIVATIVES

В. П. Зайцев, Н. М. Михайлова, И. К. Айриян, Е. В. Галкина, В. Д. Голубев, Е. В. Никитина, Ф. И. Зубков, А. В. Варламов
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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


Keywords


furfurylamines; isoindolones; maleic anhydride; [4+2] cycloaddition

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