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Synthesis of 4,5-dih ydrofuran derivatives by the reaction of acetylace tone with conjugated alkenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of the acetylacetonyl radical (generated from acetylacetone by the action of manganese acetate) with vinylacetylene, 2-vinylfuran, and butadiene Was studied. The reaction proceeds nonregioselectively with vinylacetylene: 3-acetyl-2-methyl-5-ethynyl- and 3-acetyl-2-methyl-5-(4′-acetyl-5′-methyl-2′-furyl)-4,5-dihydrofurans in a ratio of 1∶2.2 were isolated. The principal products in the reaction with 2-vinylfuran and butadiene were 3-acetyl-2-methyl-5-(2′-furyl)- and 3-acetyl-2-methyl-5-vinyl-4,5-dihydrofurans.

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Authors and Affiliations

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

    G. G. Melikyan, D. A. Mkrtchyan & Sh. O. Badanyan

Authors
  1. G. G. Melikyan
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  2. D. A. Mkrtchyan
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  3. Sh. O. Badanyan
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Additional information

Communication 62 from the series “Reactions of unsaturated compounds.” See [1] for communication 61.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 884–887, July, 1980.

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Melikyan, G.G., Mkrtchyan, D.A. & Badanyan, S.O. Synthesis of 4,5-dih ydrofuran derivatives by the reaction of acetylace tone with conjugated alkenes. Chem Heterocycl Compd 16, 678–680 (1980). https://doi.org/10.1007/BF00557734

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  • DOI: https://doi.org/10.1007/BF00557734

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