Title: | Microwave-Assisted Multicomponent Synthesis of Dihydroquinoxalinones on Soluble Polymer Support |
Authors: | Dalvi, Prashant B. Lin, Shu-Fen Paike, Vijaykumar Sun, Chung-Ming 應用化學系 Department of Applied Chemistry |
Keywords: | dihydroquinoxalin-2-ones;microwave chemistry;soluble supported synthesis;multicomponent reaction (MCR) |
Issue Date: | 1-Jul-2015 |
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. |
URI: | http://dx.doi.org/10.1021/acscombsci.5b00053 http://hdl.handle.net/11536/128065 |
ISSN: | 2156-8952 |
DOI: | 10.1021/acscombsci.5b00053 |
Journal: | ACS COMBINATORIAL SCIENCE |
Volume: | 17 |
Begin Page: | 421 |
End Page: | 425 |
Appears in Collections: | Articles |