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Synthesis of 5-substituted furans on the basis of the reactions of 1,3-alkadiynes with Β-dicarbonyl compounds

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 1,3-hexadiyne, 1,3-heptadiyne, and 1,3-octadiyne with acetylacetone and acetoacetic ester in the presence of manganese(III) and copper(II) acetates proceeds with the participation of both triple bonds and leads to substituted 5-alkynyl- and 5-(5-furyl)furans: in the case of 5-hydroxy-5-methyl-1,3-hexadiyne the terminal triple bond participates selectively in the process as a result of the effective protection of the disubstituted triple bond by the dimethylhydroxymethyl group.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, 375094, Erevan

    G. G. Melikyan, A. B. Sargsyan & Sh. O. Badanyan

Authors
  1. G. G. Melikyan
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  2. A. B. Sargsyan
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  3. Sh. O. Badanyan
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Additional information

Communication 148 in the series “Reactions of unsaturated compounds”; see [1] for Communication 147.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 738–742, June, 1989.

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Melikyan, G.G., Sargsyan, A.B. & Badanyan, S.O. Synthesis of 5-substituted furans on the basis of the reactions of 1,3-alkadiynes with Β-dicarbonyl compounds. Chem Heterocycl Compd 25, 606–609 (1989). https://doi.org/10.1007/BF00470014

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  • DOI: https://doi.org/10.1007/BF00470014

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