title: 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 α-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.
authors.affiliation: †Department of Applied Chemistry, National Chiao-Tung University, 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Prashant B
authors.initials: PB
authors.lastname: Dalvi
authors.affiliation: †Department of Applied Chemistry, National Chiao-Tung University, 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.|‡Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100, Shih-Chuan First Road, Kaohsiung 807-08, Taiwan.
authors.forename: Shu-Fen
authors.initials: SF
authors.lastname: Lin
authors.affiliation: †Department of Applied Chemistry, National Chiao-Tung University, 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Vijaykumar
authors.initials: V
authors.lastname: Paike
authors.affiliation: †Department of Applied Chemistry, National Chiao-Tung University, 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.|‡Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100, Shih-Chuan First Road, Kaohsiung 807-08, Taiwan.
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001565:Benzoates; D003486:Cyanides; D004952:Esters; D011108:Polymers; D011810:Quinoxalines
keywords: dihydroquinoxalin-2-ones; microwave chemistry; multicomponent reaction (MCR); soluble supported synthesis