电子推拉调制：底物控制区域选择性开关在1,3-偶极环加成的isatin衍生亚甲基酰与查尔酮

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-24 DOI:10.1016/j.tet.2025.134865

Shubham Dashora , Anirban Chowdhury , Dhruvisha Kiritbhai Patel , Uma Mahesh Addala , Srinu Tothadi , Keshav Lalit Ameta

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引用次数: 0

摘要

通过调节1,3-偶极环加成，通过isatin衍生的原位生成的azomiine ylides与查尔酮合成螺旋吡咯烷-氧吲哚类似物，实现了区域选择性的切换。酮端上的吸电子基团和醛端上的中性或吸电子基团有利于β攻击。相反，醛端上的给电子基团将选择性转向α-攻击。区域异构体的结构已通过核磁共振、质谱和SC-XRD测定。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Electron pull-push modulation: Substrate controlled regioselectivity switch in 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with chalcones

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Electron pull-push modulation: Substrate controlled regioselectivity switch in 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with chalcones

A switch in regioselectivity has been achieved by modulating electron pull and push during the synthesis of spiropyrrolidine-oxindole analogs through 1,3-dipolar cycloaddition of isatin derived in-situ generated azomethine ylides with chalcones. Electron-withdrawing groups on ketone termini, along with neutral or electron-withdrawing groups on aldehyde termini, favored β-attack. In contrast, electron-donating groups on aldehyde termini switch the selectivity to α-attack. Structures of regioisomers have been determined by NMR, HRMS and SC-XRD.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.