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.
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This work was carried out with the financial support of the Russian Foundation for Basic Research (Grant 11-03-90416 Ukr_f_a).
The authors express their gratitude to the laboratory staff of the Precision instrumental methods of analysis department "PRIMA" of the Shared Research and Education Center of the Peoples' Friendship University of Russia.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, pp. 538-548, March, 2012.
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Zaytsev, V.P., Mikhailova, N.M., Airiyan, I.K. et al. Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives. Chem Heterocycl Comp 48, 505–513 (2012). https://doi.org/10.1007/s10593-012-1023-1
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DOI: https://doi.org/10.1007/s10593-012-1023-1