Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 48, Issue 3, Pages 505-513Publisher
SPRINGER
DOI: 10.1007/s10593-012-1023-1
Keywords
furfurylamines; isoindolones; maleic anhydride; [4+2] cycloaddition
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Funding
- Russian Foundation for Basic Research [11-03-90416 Ukr_f_a]
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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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