Microwave-Assisted Multicomponent Synthesis of Dihydroquinoxalinones on Soluble Polymer Support

Abstract

A one-pot and two-step reaction of four components, including aldehydes, Fmoc-protected alpha-amino acid, isocyanide, and soluble polymer-supported 4-fluoro-3-amino benzoate ester, was developed for an efficient synthesis of dihydroquinoxalinones under microwave irradiation. Fmoc deprotection followed by intramolecular cyclization of the diamide gave a facile access to novel bicyclic quinoxalin-2-ones. On the basis of this approach, a new route to synthesize this privileged scaffold from the diamide intermediate was designed and accomplished with high yields. Use of multicomponent reaction (MCR) has been shown to display a good functional group tolerance, while the product isolation and purification is straightforward by precipitation and washings. Current library discusses the synthesis and diversification of 21 compounds produced using this strategy.