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Reaction of 1-substituted tetrahydro-β-carbolines with activated alkynes-a new original approach to the synthesis of tetrahydroazocino[5,4-b]indoles

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Abstract

The transformations of 1-substituted tetrahydro-β-carbolines by the action of activated alkynes were studied. The action of dimethyl acetylenedicarboxylate in methanol gives products of the opening of the tetrahydropyridine fragment, namely, 2-methoxyalkylindoles. The action of ethyl propiolate in ethanol and of tosylacetylene in methanol gives mixtures of azocino[5,4-b]indoles and 2-alkoxyindoles. The action of ethyl propiolate in acetonitrile gives azocinoindoles.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 703–715, May, 2007.

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Voskressensky, L.G., Borisova, T.N., Kulikova, L.N. et al. Reaction of 1-substituted tetrahydro-β-carbolines with activated alkynes-a new original approach to the synthesis of tetrahydroazocino[5,4-b]indoles. Chem Heterocycl Compd 43, 587–598 (2007). https://doi.org/10.1007/s10593-007-0093-y

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  • DOI: https://doi.org/10.1007/s10593-007-0093-y

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