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

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

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24 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)9682-9692
Number of pages11
JournalJournal of Organic Chemistry
Volume82
Issue number18
DOIs
StatePublished - Sep 15 2017
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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