Abstract
A new heterocyclic system — 3-imino-4-methyldihydrothieno[3,4-b]indole — was obtained by treatment of 1-methylindole-2-carboxylic acid thioamide with aldehydes or ketones in the presence of hydrogen chloride. Reactions involving saponification and acetylation of the imino group of the thieno ring and opening of the thieno ring by the action of LiAlH4 to give a bis(indolylphenylmethyl) sulfide were carried out. A scheme is proposed in which the SH group of the thioamide adds to the carbonyl compound in the first step, after which the product undergoes intramolecular cyclization in the 3 position of indole.
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L. A. Aksanova, N. R. Kucherova, and V. A. Zagorevskii, Zh. Obshch. Khim., 34, 1609 (1964).
N. A. Kogan and M. I. Vlasova, Khim. Geterotsikl. Soedin., No. 11, 1516 (1976).
N. A. Kogan, Khim. Geterotsikl Soedin., No. 4, 504 (1975).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1327–1331, October, 1977.
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Kogan, N.A. Synthesis of dihydrothieno[3,4-b]indoles. Chem Heterocycl Compd 13, 1061–1065 (1977). https://doi.org/10.1007/BF00480136
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DOI: https://doi.org/10.1007/BF00480136