Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines

被引：0

作者：

Zhou, Pengyu ^{[1
]}

Zhang, Tiantian ^{[1
]}

Lu, Qing ^{[2
]}

Xie, Yujuan ^{[1
]}

Huang, Liliang ^{[1
]}

Feng, Huangdi ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, Shanghai 201620, Peoples R China

[2] Bide Pharmatech Co Ltd, Shanghai 200433, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; FUNCTIONALIZED PYRROLES; SELECTIVE SYNTHESIS; TERMINAL ALKYNES; BETA-ENAMINONES; CYCLOADDITION; ANNULATION; ALDEHYDES;

D O I：

10.1021/acs.joc.4c02198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compared with the well-developed cyclization of functionalized propargylamines, the use of unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted pyrroles via a DBU-mediated intramolecular cycloaddition of N-alkyl propargylamines. This reaction employs cyclization to access dihydropyrrole intermediates, followed by oxidation to produce pyrroles in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, a broad substrate scope, high atom economy, high selectivity, and simple operation are also advantages of this protocol.

引用

页数：7

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