Synthetic exploitation of halogenated alkenes containing an electron-withdrawing group: synthesis of alpha-chlorohydrazones and ketene aminals by regiospecific reactions of in situ generated imide chlorides

Abstract

A concise approach for the construction of ketene aminals and alpha-chlorohydrazones has been developed. It involves reactions of the regiodefined gem-dihalo nitrovinyl compound of in situ generated imide chlorides in different media with primary arylamines being dependent on the aryl groups. A range of ketene aminals and alpha-chlorohydrazones are obtained in good to high yields. In addition, alpha-aminohydrazones are prepared by using alpha-chlorohydrazones as the precursors. (C) 2014 Elsevier Ltd. All rights reserved.