通过 Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles 串联合成多取代吡咯

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-03-11 DOI:10.1021/acs.joc.4c0307110.1021/acs.joc.4c03071

Anup Kumar Sharma, Mahesh Kumar, Shiv Chand and Krishna Nand Singh*,

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引用次数: 0

摘要

在回流条件下，利用Cu(MeCN)4BF4和Ag2CO3在甲苯中串联环化α-氧烯酮- n， s -缩醛和β-酮二腈，探索了一种多功能化吡咯的新方法。该反应涉及C-C / C-N键的形成，并被认为是通过烯胺形成，分子内环化和重排进行的。该方法的潜力也被证明是克级反应以及一些有用的有机转化。该反应为制备底物范围广、官能团耐受性好的多取代吡咯提供了一条实用途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

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Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)₄BF₄ and Ag₂CO₃ in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, and is assumed to proceed via enamine formation, intramolecular cyclization, and rearrangement. The potential of the methodology has also been demonstrated for a gram-scale reaction as well as for some useful organic transformations. The reaction offers a practical pathway to achieve polysubstituted pyrroles with broad substrate scope and good functional group tolerance.

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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.