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Issue 10, 1996
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Formation of polyheterocyclic systems by reaction of 2-imino-4-methyl-2H-1-benzopyran-3-carbonitrile with active methylene compounds

Abstract

2-Imino-4-methyl-2H-1-benzopyran-3-carbonitrile undergoes [1,5] tautomerism in solution to 2-amino-4-methylidene-4H-1-benzopyran-3-carbonitrile. Reaction with one equivalent of compounds containing a reactive methylene group affords simple 4-methylbenzopyran derivatives, and a methylidene derivative (of [1]benzopyrano[2,3-b][1,8]naphthyridine). Reaction with two and three equivalents of malononitrile affords derivatives of [1]benzopyrano[2,3,4-de]quinoline and [1]benzopyrano[2,3,4-de][1,6]-naphthyridine, which had previously been formulated as bicyclic benzopyran derivatives. The X-ray crystal structure of ethyl 3-amino-2-cyano-3-(2-imino-4-methyl-2H-1-benzopyran-3-yl)prop-2-enoate has been determined, showing the presence of two molecules in the asymmetric unit.

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Article type: Paper
DOI: 10.1039/P19960001067
Citation: J. Chem. Soc., Perkin Trans. 1, 1996,0, 1067-1071
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    Formation of polyheterocyclic systems by reaction of 2-imino-4-methyl-2H-1-benzopyran-3-carbonitrile with active methylene compounds

    C. N. O'Callaghan, T. B. H. McMurry, J. E. O'Brien, S. M. Draper and D. J. Wilcock, J. Chem. Soc., Perkin Trans. 1, 1996, 0, 1067
    DOI: 10.1039/P19960001067

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