Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

被引：18

作者：

Pal, Arpal ^{[1
]}

Koduri, Naga D. ^{[1
]}

Wang, Zhiguo ^{[1
]}

Quiroz, Erika Lopez ^{[1
]}

Chong, Alexandra ^{[1
]}

Vuong, Matthew ^{[1
]}

Rajagopal, Nisha ^{[1
]}

Nguyen, Michael ^{[1
]}

Roberts, Kenneth P. ^{[1
]}

Hussaini, Syed R. ^{[1
]}

机构：

[1] Univ Tulsa, Dept Chem & Biochem, 800 S Tucker Dr, Tulsa, OK 74104 USA

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 06期

基金：

美国国家科学基金会;

关键词：

Enaminone; Copper; Heterocycle; Diazocarbonyl compounds; Cross-coupling; SULFIDE CONTRACTION; N-TOSYLHYDRAZONES; BETA-ENAMINONES; DIAZO-COMPOUNDS; RING CLOSURE; DERIVATIVES; EFFICIENT; ACID; CHROMOPHORE; ALKALOIDS;

D O I：

10.1016/j.tetlet.2017.01.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of operationally simple and cost-effective methods for C-C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted alpha-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with alpha-diazodiesters, alpha-diazoketoesters, zodiketones, alpha-diazoketoamides, alpha-diazoesteramides, alpha-diazoketosulfones and alpha-diazomonoketones. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：586 / 589

页数：4

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