Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

被引：42

作者：

Dai, Haican ^{[1
]}

Yu, Sisi ^{[1
]}

Cheng, Wanli ^{[1
]}

Xu, Ze-Feng ^{[1
]}

Li, Chuan-Ying ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 48期

基金：

中国国家自然科学基金;

关键词：

ALPHA-DIAZOCARBONYL COMPOUNDS; C-H ACTIVATION; ALPHA; BETA-UNSATURATED IMINES; AZAVINYL CARBENES; ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; RING EXPANSION; N-SULFONYL-1,2,3-TRIAZOLES; TRANSANNULATION; 1,2,3-TRIAZOLES;

D O I：

10.1039/c7cc02521a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of alpha-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

引用

页码：6417 / 6420

页数：4

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