Selected Electrosynthesis of 3-Aminopyrazoles from α,β-Alkynic Hydrazones and Secondary Amines

J Org Chem. 2024 May 3;89(9):6520-6526. doi: 10.1021/acs.joc.3c02995. Epub 2024 Apr 11.

Abstract

An available and simple electromediated cyclization method for 3-amino-substituted pyrazoles by using α,β-alkynic hydrazone and secondary amine is described. The strategy utilizes KI as an electrolyte in an undivided cell with a constant current, generating the desired products in moderate-to-good yield. The method features selective amination at the 3-position of the pyrazole skeleton. The results indicate that α,β-alkynic hydrazones functionalized with aromatic groups and secondary amines functionalized with electron-rich groups were better tolerated in this transformation.