Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

Tienan Jin; Fukuzou Kitahara; Shin Kamijo; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2008.02.115

Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

Tienan Jin, Fukuzou Kitahara, Shin Kamijo, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

184 Citations (Scopus)

Abstract

The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a Cu^I catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

Original language	English
Pages (from-to)	2824-2827
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.115
Publication status	Published - 2008 Apr 21

Keywords

5-Substituted 1H-tetrazole
Copper azide
Copper catalyst
Nitrile
Trimethylsilyl azide
[3+2] Cycloaddition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.02.115

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abstract = "The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a CuI catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.",

keywords = "5-Substituted 1H-tetrazole, Copper azide, Copper catalyst, Nitrile, Trimethylsilyl azide, [3+2] Cycloaddition",

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AU - Jin, Tienan

AU - Kitahara, Fukuzou

AU - Kamijo, Shin

AU - Yamamoto, Yoshinori

PY - 2008/4/21

Y1 - 2008/4/21

N2 - The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a CuI catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

AB - The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a CuI catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

KW - 5-Substituted 1H-tetrazole

KW - Copper azide

KW - Copper catalyst

KW - Nitrile

KW - Trimethylsilyl azide

KW - [3+2] Cycloaddition

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Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

Abstract

Keywords

ASJC Scopus subject areas

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