Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow

被引：33
|
作者：
Rassokhina, Irina V. [3 ]
Tikhonova, Tatyana A. [3 ]
Kobylskoy, Sergey G. [1 ]
Babkin, Igor Yu. [1 ]
Shirinian, Valerii Z. [3 ]
Gevorgyan, Vladimir [2 ]
Zavarzin, Igor V. [3 ]
Volkova, Yulia A. [3 ]
机构：
[1] Lab High Technol Ltd, 86 Prosp Vernadskogo, Moscow 119571, Russia
[2] Univ Illinois, Dept Chem, 845 West Taylor St,Room 4500, Chicago, IL 60607 USA
[3] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 18期
关键词：
HIGH-TEMPERATURE/PRESSURE CONDITIONS; ORGANIC-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; MANNICH REACTIONS; TANDEM REACTIONS; AMINE SYNTHESIS; CHEMISTRY; DERIVATIVES; CYCLIZATION;
D O I：
10.1021/acs.joc.7b01762
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward method for the synthesis of functionalized imidazo[2,1-b]thiazoles starting from benzalde-hydes, 2-aminothiazoles, and alkynes under copper(I,II) catalysis was developed. The protocol allows the construction of a variety of aryl-substituted imidazo[2,1-b]benzothiazoles, -[2,1-b]thiazoles, and -[2,1-b][1,3,4]thiadiazoles. The reactions were easy to perform affording most of the desired products in 33-93% yields. The intensification of the process in a continuous-flow reactor increases the products' yields up to quantitative.
引用
收藏
页码：9682 / 9692
页数：11
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