Synthesis and some transformations of 5-isoxazolylsulfonyl chlorides

Authors

  • P. S. Lebed Enamine Ltd., Ukraine
  • A. O. Tolmachov Enamine Ltd., Ukraine
  • Yu. O. Zubchuk Ukr Org Syntez Ltd. (UORSY), Ukraine
  • O. M. Boyko Kyiv National Taras Shevchenko University, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.17.922

Keywords:

N-hydroxyimidoyl chlorides, benzylethynyl sulfide, 5-(benzylthio)-3-isoxazoles, oxidative chlorination, isoxazole-5-sulfonylchlorides

Abstract

The effect of the structure of 5-(benzylthio)isoxazoles on selectivity of the synthesis of 5-(chlorosulfonyl)isoxazoles has been determined. The chemical behavior in relation to amines has been described.

Aim. To develop the methods for the synthesis of 5-(chlorosulfonyl)- isoxazoles and 4-chloro-5-(chlorosulfonyl)isoxazoles as promising reagents for construction of prospective bioactive compounds.

Results and discussion. The number of 5-(benzylthio)isoxazoles was obtained by cyclocondensation of N-hydroxyimidoyl chlorides or 2-chloro-2-(hydroxyimino) acetates with benzylethynylsulfide. Their oxidative chlorination with gaseous chlorine led to formation of the mixture of isoxazole-5-sulfonyl chlorides and 4-chloroisoxazole-5-sulfonyl chlorides. The ratio between these products in the mixture depended on the nature of the substitution group in position 3 of the isoxazole ring. For the synthesis of 4-chloro-5-(chlorosulfonyl)isoxazoles with acceptable yields the approach of an advance chlorination of 5-benzylthioisoxazoles by N-chlorosuccinimide with further oxidative chlorination was used.

Experimental part. The synthesis of the starting and target compounds was performed in classic preparative conditions; flesh-chromatography; elemental analysis; LCMS; 1H and 13C NMR-spectroscopy were used.

Conclusions. The reaction of oxidative chlorination of 5-(benzylthio)-3-isoxazoles has been studied. The synthetic approach for the previously unknown representatives of isoxazole-5-sulfonylchlorides has been developed.

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Published

2017-09-15

How to Cite

(1)
Lebed, P. S.; Tolmachov, A. O.; Zubchuk, Y. O.; Boyko, O. M.; Vovk, M. V. Synthesis and Some Transformations of 5-Isoxazolylsulfonyl Chlorides. J. Org. Pharm. Chem. 2017, 15, 40-47.

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Original Researches