α-Anilinoketones, esters and amides: A chemical study

Abstract

A group of α-anilinoketones, 2-aminoalcohols, α-anilinoesters and α-anilinoamides were successfully synthesized and characterized by NMR spectroscopy and mass spectrometry. The yields were, in general, moderate to good (up to 75.4%), except for the α-anilinoesters (16.9-35.6%). The α-halocarbonyl starting materials showed different chemical reactivities. α-Haloketones and α-chloroacetates afforded monoalkylation, while small α-chloroamides afforded dialkylation. Finally, NMR spectroscopy revealed interesting structural features about the 2-aminoalcohols and diphenylamides. © 2012 by the authors; licensee MDPI, Basel, Switzerland.