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

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

[Display omitted] 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, e...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 56; no. 50; pp. 7020 - 7023
Main Authors: Lisakova, Anna D., Ryabukhin, Dmitry S., Trifonov, Rostislav E., Ostrovskii, Vladimir A., Vasilyev, Aleksander V.
Format: Journal Article
Language:English
Published: Elsevier Ltd 16-12-2015
Subjects:
Alcohols
Alkylation
Tetrazoles
Tetrazolium ions
Trifluoromethanesulfonic acid
Trifluoromethanesulfonic acid
Tetrazoles
Tetrazolium ions
Alkylation
Alcohols
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Summary:[Display omitted] 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 0.3–12h to afford 2-alkyl-2H-tetrazoles in 30–98% yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.11.005