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Reactions of 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones with some nucleophilic reagents

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Abstract

Reactions of 2-bromo-1-phenyl- and 2-bromo-1-(4-methylphenyl)-3,4,4-trichlorobut-3-en-1-ones with morpholine and diethylamine are accompanied by prototropic allylic rearrangement, leading to 3-amino-1-aryl-2-bromo-4,4-dichlorobut-2-en-1-ones as mixtures of E and Z isomers. The title compounds react with hydrazine, hydroxylamine, and thiourea to give the corresponding 5-aroyl-4-methoxypyrazoles, 3-aryl-5-hydroxyiminomethyl-4-methoxyisoxazoles, and 2-amino-4-aryl-5-trichlorovinylthiazoles.

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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

    V. I. Potkin, S. K. Petkevich & P. V. Kurman

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  1. V. I. Potkin
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  2. S. K. Petkevich
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  3. P. V. Kurman
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Correspondence to V. I. Potkin.

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Original Russian Text © V.I. Potkin, S.K. Petkevich, P.V. Kurman, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 11, pp. 1626–1632.

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Potkin, V.I., Petkevich, S.K. & Kurman, P.V. Reactions of 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones with some nucleophilic reagents. Russ J Org Chem 43, 1622–1627 (2007). https://doi.org/10.1134/S1070428007110061

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  • DOI: https://doi.org/10.1134/S1070428007110061

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