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.

The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported. The formation of a transient diazonium species with a dinitrite...

The synthesis of disubstituted tetrazoles is described from 1H-5-monosubstituted tetrazoles via the aliphatic amine diazotization reaction, which forms a transient alkyl diazonium intermediate, acting as an alkylating agent. Although the...

In this paper, the synthesis of alkyl aryl ethers from electron poor phenols and amines, using 1,3-propanedinitrite, is described. Due to the mild conditions, functionalized primary, secondary, and tertiary alkyl groups were successfully introduced, denoting a highly tolerant process that allows for unprotected alcohols and acetals. The reaction is thought to proceed through the formation of a diazonium intermediate that undergoes subsequent SN2 or SN1 reactions.