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Synthesis of 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides from 1-aryl-3,4,4-trichlorobut-3-en-1-ones

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Abstract

The reaction of 1-aryl-3,4,4-trichlorobut-3-en-1-ones with semicarbazide hydrochloride in the presence of sodium acetate is accompanied by prototropic allylic rearrangement, leading to the formation of two isomeric products, semicarbazones of the initial ketones and 1-aryl-3,4,4-trichlorobut-2-en-1-one semicarbazones. The latter undergo heterocyclization in the presence of triethylamine to give the corresponding 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    S. K. Petkevich, V. I. Potkin & R. V. Kaberdin

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  1. S. K. Petkevich
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  2. V. I. Potkin
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  3. R. V. Kaberdin
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Original Russian Text © S.K. Petkevich, V.I. Potkin, R.V. Kaberdin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 10. pp. 1496–1499.

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Petkevich, S.K., Potkin, V.I. & Kaberdin, R.V. Synthesis of 3-aryl-5-dichloromethyl-1H-pyrazole-1-carboxamides from 1-aryl-3,4,4-trichlorobut-3-en-1-ones. Russ J Org Chem 42, 1481–1485 (2006). https://doi.org/10.1134/S1070428006100149

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  • DOI: https://doi.org/10.1134/S1070428006100149

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