期刊
ACS COMBINATORIAL SCIENCE
卷 17, 期 7, 页码 421-425出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.5b00053
关键词
dihydroquinoxalin-2-ones; microwave chemistry; soluble supported synthesis; multicomponent reaction (MCR)
资金
- National Science Council of Taiwan
- Centre for Bioinformatics Research of Aiming for the Top University Plan of the National Chiao Tung University
- Ministry of Education, Taiwan
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.
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