Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

被引：53

作者：

Zhu, Zhongzhi ^{[1
]}

Tang, Xiaodong ^{[1
]}

Cen, Jinghe ^{[1
]}

Li, Jianxiao ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 30期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; VINYL AZIDES; POTASSIUM THIOCYANATE; EFFICIENT SYNTHESIS; CASCADE ANNULATION; INTERNAL OXIDANTS; DERIVATIVES; ACCESS; INHIBITORS; 2-AMINOTHIAZOLES;

D O I：

10.1039/c8cc00445e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.

引用

页码：3767 / 3770

页数：4

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