Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01762

DOI: 10.1021/acs.joc.7b01762

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