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Issue 0, 1966
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Rearrangement reactions of dimethyl 2,7-dimethyl-3H-azepine-3,6-dicarboxylate

Abstract

The base-catalysed reaction of dimethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate to derivatives of both 4H- and 3H-azepines can be reversed by hydrochloric acid. Dimethyl 2,7-dimethyl-3H-azepine-3,6-dicarboxylate rearranges to methyl (5-methoxycarbonyl-2,6-dimethyl-3-pyridyl)acetate under the action of either sodium methoxide or mineral acids. With ethanolic hydrochloric acid, two other products have been identified from the azepinedicarboxylate, the original 4-chloromethyl-1,4-dihydropyridine and a hydroxy-dihydroazepine. The action of N-bromosuccinimide on dimethyl 4,5-dihydro-2,7-dimethyl-1H-azepine-3,6-dicarboxylate yields a lactone formed by bromination of a nuclear methyl group followed by cyclisation with an adjacent ester group.

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Article type: Paper
DOI: 10.1039/J39660001075
J. Chem. Soc. C, 1966, 1075-1078

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    Rearrangement reactions of dimethyl 2,7-dimethyl-3H-azepine-3,6-dicarboxylate

    M. Anderson and A. W. Johnson, J. Chem. Soc. C, 1966, 1075
    DOI: 10.1039/J39660001075

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