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

doi:10.1021/acs.joc.7b01762

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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33 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 language	English (US)
Pages (from-to)	9682-9692
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	82
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.7b01762
State	Published - Sep 15 2017
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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@article{9edba9dec08e42079c142ec44239bc0b,

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

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.",

author = "Rassokhina, {Irina V.} and Tikhonova, {Tatyana A.} and Kobylskoy, {Sergey G.} and Babkin, {Igor Yu} and Shirinian, {Valerii Z.} and Vladimir Gevorgyan and Zavarzin, {Igor V.} and Volkova, {Yulia A.}",

note = "Funding Information: High-resolution mass spectra were recorded at the Department of Structural Studies of the Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow. The reported study was funded by the RFBR and Moscow city Government according to the research project no. 15-34-70030.",

year = "2017",

month = sep,

day = "15",

doi = "10.1021/acs.joc.7b01762",

language = "English (US)",

volume = "82",

pages = "9682--9692",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A3-Coupling in Batch and Continuous Flow

AU - Rassokhina, Irina V.

AU - Tikhonova, Tatyana A.

AU - Kobylskoy, Sergey G.

AU - Babkin, Igor Yu

AU - Shirinian, Valerii Z.

AU - Gevorgyan, Vladimir

AU - Zavarzin, Igor V.

AU - Volkova, Yulia A.

N1 - Funding Information: High-resolution mass spectra were recorded at the Department of Structural Studies of the Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow. The reported study was funded by the RFBR and Moscow city Government according to the research project no. 15-34-70030.

PY - 2017/9/15

Y1 - 2017/9/15

N2 - 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.

AB - 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.

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ER -

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

Abstract

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