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Abstract <p>A procedure has been proposed for the regioselective synthesis of new 1,2,3-triazole derivatives from methyl alka-2,3-dienoates. The effect of substituents in the initial reactants on the regio- and stereo­selectivity of the reaction has been studied, and the synthesized compounds have been characterized by physicochemical methods. Regioselective 1,3-dipolar cycloaddition of 5-(azidomethyl)furfural [prepared from 5-(chloromethyl)furfural] to alka-2,3-dienoates containing a cyclic imide fragment in toluene afforded substituted 1,2,3-triazoles with maximum remoteness of the furfuryl and ester groups from each other, which minimizes steric repulsion.</p>

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Regioselective Synthesis of Furfuryl-Substituted 1,2,3-Triazoles by 1,3-Dipolar Cycloaddition of 5-(Azidomethyl)furfural to Methyl Alka-2,3-dienoates

  • 期刊论文

  • 发表日期：

    2025年7月1日

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  • G. M. Gindullina,
  • G. F. Sakhautdinova,
  • I. M. Sakhautdinov

摘要

Abstract

A procedure has been proposed for the regioselective synthesis of new 1,2,3-triazole derivatives from methyl alka-2,3-dienoates. The effect of substituents in the initial reactants on the regio- and stereo­selectivity of the reaction has been studied, and the synthesized compounds have been characterized by physicochemical methods. Regioselective 1,3-dipolar cycloaddition of 5-(azidomethyl)furfural [prepared from 5-(chloromethyl)furfural] to alka-2,3-dienoates containing a cyclic imide fragment in toluene afforded substituted 1,2,3-triazoles with maximum remoteness of the furfuryl and ester groups from each other, which minimizes steric repulsion.