Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF3SO3H

doi:10.1016/j.tetlet.2015.11.005

Tetrahedron Letters

Volume 56, Issue 50, 16 December 2015, Pages 7020-7023

https://doi.org/10.1016/j.tetlet.2015.11.005 Get rights and content

Abstract

Reactions of 5-substituted NH-tetrazoles with alcohols in the superacid CF₃SO₃H have been studied. Both the structure of the tetrazole and the nature of alcohol were found to dramatically influence the selectivity of the reaction and yields of products. Tetrazoles bearing phenyl, electron-donating aryl, or benzyl groups at the 5-position, have been alkylated using various alcohols (including MeOH and EtOH) in CF₃SO₃H upon heating at 60 °C for 0.3–12 h to afford 2-alkyl-2H-tetrazoles in 30–98% yields.

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Acknowledgements

This work was supported by the Russian Foundation for Basic Research – Russia (project 15-03-02936-a) and by Saint Petersburg State University – Russia (project 12.38.195.2014). The spectral studies of the obtained compounds were carried out at the Centre for Magnetic Resonance, and the Centre for Chemical Analysis and Materials of Saint Petersburg State University.

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Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF3SO3H

Abstract

Graphical abstract

Section snippets

Acknowledgements

Bioorg. Med. Chem.

Russ. Chem. Bull., Int. Ed.

Heterocycles

Alkylation of 5-substituted NH-tetrazoles by alcohols in the superacid CF₃SO₃H