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Improved Synthesis of 5-(Chloromethyl)isoxazoles from Aldoximes and 2,3-Dichloropropene

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Abstract

Cycloaddition of nitrile oxides generated in situ from aldoximes to 2,3-dichloroprop-1-ene in the oxidizing system Oxone®–NaCl–Na2CO3 in aqueous medium afforded 3-organyl-5-(chloromethyl)isoxazoles. The procedure provides high yields of the target products and avoids the use of organic oxidants, bases, and solvents.

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ACKNOWLEDGMENTS

The authors thank the Baikal Analytical Center of collective use (Siberian Branch, Russian Academy of Sciences) for the equipment.

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    A. N. Shilova, N. S. Shatokhina & E. V. Kondrashov

  2. Irkutsk State University, 664003, Irkutsk, Russia

    A. N. Shilova

Authors
  1. A. N. Shilova
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  2. N. S. Shatokhina
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  3. E. V. Kondrashov
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Correspondence to E. V. Kondrashov.

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The authors declare the absence of conflict of interest.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 10, pp. 1123–1128 https://doi.org/10.31857/S0514749222100123.

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Shilova, A.N., Shatokhina, N.S. & Kondrashov, E.V. Improved Synthesis of 5-(Chloromethyl)isoxazoles from Aldoximes and 2,3-Dichloropropene. Russ J Org Chem 58, 1554–1558 (2022). https://doi.org/10.1134/S1070428022100268

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