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<p>Xanthenone fused spiro-pyrrolidine oxindoles were conveniently synthesized in good yields with high regio- and diastereoselectivity from a multicomponent synthesis involving tetrahydroxanthenones, α-amino acids, and isatins via an azomethine ylide based [3 + 2] cycloaddition process. We utilized tetrahydroxanthenone as a dipolarophile for the first time in the [3 + 2] cycloaddition of decarboxylated azomethine ylide. The relative configuration of the spirocycloadduct was determined by single-crystal X-ray diffraction analysis.</p> Graphical abstract <p>We have developed a straightforward protocol for the regio and diastereoselective synthesis of xanthenone fused spiro pyrrolidine oxindoles via MC-1,3 DCA, utilizing tetrahydroxanthenoe in azomethine ylide cycloaddition through decarboxylation.</p> <p></p>

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Synthesis of xanthenone fused spiro pyrrolidine oxindoles via multicomponent [3 + 2] cycloaddition reactions

  • 期刊论文

  • 发表日期：

    2025年3月21日

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  • Gurusivam Paramasivam,
  • Baskaralingam Palanichamy,
  • Nagaraaj Paramathevar

摘要

Xanthenone fused spiro-pyrrolidine oxindoles were conveniently synthesized in good yields with high regio- and diastereoselectivity from a multicomponent synthesis involving tetrahydroxanthenones, α-amino acids, and isatins via an azomethine ylide based [3 + 2] cycloaddition process. We utilized tetrahydroxanthenone as a dipolarophile for the first time in the [3 + 2] cycloaddition of decarboxylated azomethine ylide. The relative configuration of the spirocycloadduct was determined by single-crystal X-ray diffraction analysis.

Graphical abstract

We have developed a straightforward protocol for the regio and diastereoselective synthesis of xanthenone fused spiro pyrrolidine oxindoles via MC-1,3 DCA, utilizing tetrahydroxanthenoe in azomethine ylide cycloaddition through decarboxylation.