Aminimides. II. A one-step synthesis of aminimides from carboxylic acid esters

Abstract

The general applicability of preparing aminimides from esters and insitu generated 1,1,1-trimethylaminimine is reported. Acyclic, alicyclic, aromatic, and heteroaromatic trimethylaminimides have been synthesized by the one-step reaction. The synthetic scheme consists of reacting an ester with a 1,1,1-trimethylhydrazinium salt in the presence of an anhydrous base such as sodium methoxide. The choice of solvent, reaction temperature, and base and the electronegativity of the acyl substituent influence the ease of aminimide formation.