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Three-Component Reaction of Sulfonamides with Acetylene and Amines

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Abstract

N-(2-Phenyl-1-piperidin-1-ylethylidene)tosylamide was synthesized by oxidative coupling of arenesulfonamides, acetylenes, and secondary amines. The reaction of phenylacetylene or propargyl alcohol with triflamide and piperidine under the same conditions unexpectedly gave N-[(1E)-piperidin-1-ylmethylidene]triflamide TfN=CHNC5H10 as a result of cleavage of the triple bond in the alkyne. A similar reaction with benzoylacetylene gave (2E)-1-phenyl-3-piperidin-1-ylprop-2-en-1-one, while triflamide did not react. Adducts of a series of acetylenes with triflamide were obtained using triflamide sodium salt. Attempted synthesis of an N-triflyl-substituted analog of amidine 1 by the reaction of benzoylacetylene with triflamide and piperidine or morpholine in the presence of Cu(OTf)2 and hydrogen peroxide as an oxidant unexpectedly gave 1-piperidin-1-yl- or 1-morpholin-1-ylmethanimine, respectively.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    B. A. Shainyan, V. I. Meshcheryakov & I. V. Sterkhova

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  1. B. A. Shainyan
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  2. V. I. Meshcheryakov
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  3. I. V. Sterkhova
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Correspondence to B. A. Shainyan.

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Russian Text © B.A. Shainyan, V.I. Meshcheryakov, I.V. Sterkhova, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 227–233.

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Shainyan, B.A., Meshcheryakov, V.I. & Sterkhova, I.V. Three-Component Reaction of Sulfonamides with Acetylene and Amines. Russ J Org Chem 55, 179–185 (2019). https://doi.org/10.1134/S107042801902009X

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  • DOI: https://doi.org/10.1134/S107042801902009X

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