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

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

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2017, Volume: 82, Number: 18, Pages: 9682-9692 Pages count : 11 DOI: 10.1021/acs.joc.7b01762

Authors

Rassokhina Irina V. ¹ , Tikhonova Tatyana A. ¹ , Kobylskoy Sergey G. ² , Babkin Igor Yu. ² , Shirinian Valerii Z. ¹ , Gevorgyan Vladimir ³ , Zavarzin Igor V. ¹ , Volkova Yulia A. ¹

Affiliations

1	RAS - Zelinsky Institute of Organic Chemistry
2	Laboratory of High Technologies, Ltd , 86 prosp. Vernadskogo, 119571 Moscow, Russia.
3	Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500, Chicago, Illinois 60607, United States

A straightforward method for the synthesis of functionalized imidazo[2,1-b]thiazoles starting from benzaldehydes, 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.

Rassokhina I.V. , Tikhonova T.A. , Kobylskoy S.G. , Babkin I.Y. , Shirinian V.Z. , Gevorgyan V. , Zavarzin I.V. , Volkova Y.A.
Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow
Journal of Organic Chemistry. 2017. V.82. N18. P.9682-9692. DOI: 10.1021/acs.joc.7b01762 WOS Scopus OpenAlex

Web of science:	WOS:000411304500042
Scopus:	2-s2.0-85029500904
OpenAlex:	W2742539834

DB	Citing
OpenAlex	45
Scopus	42
Web of science	39