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Issue 0, 1972
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Addition reactions of heterocyclic compounds. Part XLVIII. Reactions of indoles with dimethyl acetylenedicarboxylate in the presence and absence of solvents

Abstract

Treatment of indole with dimethyl acetylenedicarboxylate alone gave a mixture from which the major components tetramethyl carbazole-1,2,3,4-tetracarboxylate, tetramethyl 9-(cis-1,2-dimethoxycarbonylvinyl)-1,2-dihydrocarbazole-1,2,3,4-tetracarboxylate, trimethyl 5,6-dihydro-6-oxophenanthridine-7,8,9-tricarboxylate and dimethyl 2,3-dihydro-2-(indol-3-yl)[1]benzazepine-3,4-dicarboxylate, and ten other indole derivatives, were isolated by chromatography and identified from their spectra. Fewer products were obtained when benzene or toluene was used as solvent; the main products in methanol and in acetic acid were, respectively, dimethyl indol-3-ylfumarate and dimethyl 2,2-di(indol-3-yl)succinate. Reactions involving 1- and 2-methylindole and diethyl acetylenedicarboxylate were also investigated.

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J. Chem. Soc., Perkin Trans. 1, 1972, 1569-1576
Article type
Paper

Addition reactions of heterocyclic compounds. Part XLVIII. Reactions of indoles with dimethyl acetylenedicarboxylate in the presence and absence of solvents

R. M. Acheson, J. N. Bridson, T. R. Cecil and A. R. Hands, J. Chem. Soc., Perkin Trans. 1, 1972, 1569
DOI: 10.1039/P19720001569

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