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Regioselective addition of hydrazines to allenylacetylenes — Convenient route to 3(5)-methyl-5(3)-substituted pyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that hydrazine hydrate, methylhydrazine, and phenylhydrazine add smoothly and regioselectively to allenylacetylenes to give 3(5)-methyl-5(3)-sub-stituted pyrazoles. In addition to the principal process, isomerization of allenylacetylenes to methyldiacetylenes, and the degree of which depends on the structure of the substrate, is observed in the reaction of methylhydrazine in an aqueous alcohol medium.

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Authors and Affiliations

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

    A. P. Khrimyan, A. V. Karapetyan & Sh. O. Badanyan

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  1. A. P. Khrimyan
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  2. A. V. Karapetyan
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  3. Sh. O. Badanyan
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Additional information

Communication 98 from the series “Reactions of unsaturated compounds.” See [1] for communication 97.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 230–238, February, 1984.

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Khrimyan, A.P., Karapetyan, A.V. & Badanyan, S.O. Regioselective addition of hydrazines to allenylacetylenes — Convenient route to 3(5)-methyl-5(3)-substituted pyrazoles. Chem Heterocycl Compd 20, 189–196 (1984). https://doi.org/10.1007/BF00506291

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  • DOI: https://doi.org/10.1007/BF00506291

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