Preparation of 1, 1-disubstituted hydrazines and their 2-acyl derivatives

Abstract

1-(1-Hydroxymethyl)benzotriazole converts 1-acyl- and 1-acyl-2-aryl-hydrazines into their 2-mono-N- or 2,2-bis-N-[(benzotriazol-1-yl)methyl] derivatives, respectively, in high yields. These adducts react readily with NaBH4, Grignard reagents, and lithium acetylides to give the corresponding 2 substituted, or 2,2-disubstituted, 1-acylhydrazines in high yields. The N-(t-butoxycarbonyl)hydrazines are readily hydrolysed offering a convenient synthetic route to 1,1-dialkyl- and 1-alkyl-1-aryl-hydrazines.