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

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED Molecular Diversity Pub Date : 2025-12-01 Epub Date: 2025-03-21 DOI:10.1007/s11030-025-11167-w

Gurusivam Paramasivam, Baskaralingam Palanichamy, Nagaraaj Paramathevar

引用次数: 0

Abstract

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.

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多组分[3 + 2]环加成反应合成杂蒽酮融合螺旋吡咯烷氧吲哚。

以四羟基蒽酮、α-氨基酸和isatins为原料，采用亚甲酰基[3 + 2]环加成工艺合成了杂蒽酮融合螺-吡咯烷氧吲哚，收率高，区域选择性和非对映选择性高。我们首次将四羟基蒽酮作为亲偶极试剂应用于脱羧亚甲酰基的[3 + 2]环加成反应中。用单晶x射线衍射分析确定了螺环加合物的相对构型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;