Alkylation of 5-Substituted 1H-Tetrazoles via the Diazotization of Aliphatic Amines.

Guillaume Reynard, Hélène Lebel

The Journal of organic chemistry 2021 Sep 03

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A new alkylation reaction of monosubstituted tetrazoles via the diazotization of aliphatic amines is reported. This method enables preferential formation of 2,5-disubstituted tetrazoles. A one-pot 1,3-dipolar cycloaddition/diazotization sequence starting from widely available nitriles is also described. Azide residues are quenched in the second step with the nitrite reagent, thus limiting the intrinsic risk associated with trimethylsilyl azide. The reaction conditions were compatible with several functional groups, including thiocyanates, which afford preferentially disubstituted 2-alkyl-5-(substituted-thio)tetrazoles.

Citation

Guillaume Reynard, Hélène Lebel. Alkylation of 5-Substituted 1H-Tetrazoles via the Diazotization of Aliphatic Amines. The Journal of organic chemistry. 2021 Sep 03;86(17):12452-12459