Divergent ionic liquid supported synthesis of isolable guanidine linked quinoxalinone and benzodiamine

Abstract

Ionic liquid supported synthesis of guanidine linked piperazine, diazepane, and aminomethylpiperidine to difluoroquinoxalinones and difluoro benzodiamine was achieved by two regioisomeric products. They were isolated from one pot reduction and intramolecular cyclization to afford quinoxalinone ring system with traceless cleavage of ionic liquid support. Besides, the ionic-supported other isomer was further cleaved in methanol. All the reactions were carried out on an ionic liquid support under various conditions to deliver biologically relevant scaffolds with high purity and excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.