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2-Diazomethyl-4-furanones. Synthesis and properties

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1,5-Bisdiazo-3-alkylpentane-2,4-diones were synthesized by the reaction of alkylmalonic acid chlorides with diazomethane; the products readily undergo intramolecular cyclization at the oxygen atom and one of the diazoacetyl groups under the influence of acidic agents with the formation of 2-diazomethyl-3-alkyl-4-furanones. It is shown that diazomethyl-4-furanones, which are vinylogs of α-diazo ketones, undergo reactions that are characteristic for aliphatic diazo compounds. The structure of the product of 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate to a diazomethyl-4-furanone was investigated by means of x-ray diffraction analysis.

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Authors and Affiliations

  1. Branch of the Institute of Chemical Physics, Academy of Sciences of the USSR, 142432, Chernogolovka

    L. A. Tolochko, A. M. Sipyagin, V. G. Kartsev, Z. G. Aliev, L. O. Atovmyan & A. T. Lebedev

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  1. L. A. Tolochko
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  2. A. M. Sipyagin
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  3. V. G. Kartsev
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  4. Z. G. Aliev
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  5. L. O. Atovmyan
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  6. A. T. Lebedev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 454–459, April, 1988.

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Tolochko, L.A., Sipyagin, A.M., Kartsev, V.G. et al. 2-Diazomethyl-4-furanones. Synthesis and properties. Chem Heterocycl Compd 24, 370–376 (1988). https://doi.org/10.1007/BF00478853

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  • DOI: https://doi.org/10.1007/BF00478853

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