区域选择性Rh（III）催化的仲芳酰胺与马来酰亚胺的螺环化和邻c (sp2)- h环：螺旋吡咯烷酮和二苯并氮杂辛酮的构建。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-29 DOI:10.1021/acs.joc.5c01089

Raju Vaggu, Marella Rosi Reddy, Mohamed Asik Ali, René Grée and Saibal Das*,

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引用次数: 0

摘要

通过弱配位酰胺羰基作为导向基团，建立了一种易于Rh（III）催化的酰胺与马来酰亚胺的螺环化和邻芳香C-H活化反应。该方案具有高竞争力，官能团耐受性和广泛的底物范围，并通过轻微调整反应条件，以中等产量提供各种螺吡咯烷三酮或取代的8元不饱和内酰胺，即偶氮嘧啶。此外，该反应具有高度的区域选择性，可生成单邻位螺和单邻位8元环状产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Regioselective Rh(III)-Catalyzed Spiro-Cyclization and ortho-C(sp2)–H-Annulations of Secondary Aromatic Amide with Maleimide: Construction of Spiropyrrolidinetriones and Dibenzoazocinetriones

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Regioselective Rh(III)-Catalyzed Spiro-Cyclization and ortho-C(sp2)–H-Annulations of Secondary Aromatic Amide with Maleimide: Construction of Spiropyrrolidinetriones and Dibenzoazocinetriones

A facile Rh(III)-catalyzed spiro-cyclization and ortho-(proximal) aromatic C–H activation reaction of amides with maleimides has been established via a weakly coordinating amide carbonyl acting as the directing group. This protocol features high competence, functional group tolerance, and wide-ranging substrate scope and, by slight adjustments of the reaction conditions, affords either a variety of spiropyrrolidinetrione or substituted 8-membered unsaturated lactams known as azocines in moderate yields. Additionally, the reaction is highly regioselective, furnishing mono-ortho-spiro and mono-ortho-8-membered annulated products.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.