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Abstract <p>The dipolar [3+2]-cycloaddition reactions of 3-aroylpyrrolo[2,1-<i>c</i>][1,4]benzothiazine-1,2,4-triones with diarylnitrones lead to the formation of benzo[<i>b</i>]isoxazolo[5',4':2,3]pyrrolo[1,2-<i>d</i>][1,4]thiazines. The reaction proceeds stereoselectively to form exclusively the (2a<i>S</i>*,3<i>R</i>*,5a<i>S</i>*) diastereomers. Density functional theory computations for the model reaction showed that the (2a<i>S</i>*,3<i>R</i>*,5a<i>S</i>*) diastereomers are both kinetically and thermodynamically preferred over the alternative (2a<i>S</i>*,3<i>S</i>*,5a<i>S</i>*) diastereomers. At room temperature in solution, the resulting cycloadducts dissociate into the starting reagents, with stability highly dependent on the electronic properties of the substituents in the nitrone moiety.</p>

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Dipolar [3+2] Cycloaddition of Nitrones to 3-Aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones

  • 期刊论文

  • 发表日期：

    2026年1月1日

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  • E. E. Khramtsova,
  • A. S. Novikov,
  • M. V. Dmitriev

摘要

Abstract

The dipolar [3+2]-cycloaddition reactions of 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones with diarylnitrones lead to the formation of benzo[b]isoxazolo[5',4':2,3]pyrrolo[1,2-d][1,4]thiazines. The reaction proceeds stereoselectively to form exclusively the (2aS*,3R*,5aS*) diastereomers. Density functional theory computations for the model reaction showed that the (2aS*,3R*,5aS*) diastereomers are both kinetically and thermodynamically preferred over the alternative (2aS*,3S*,5aS*) diastereomers. At room temperature in solution, the resulting cycloadducts dissociate into the starting reagents, with stability highly dependent on the electronic properties of the substituents in the nitrone moiety.