Scaffold-directed and traceless synthesis of tricyclic quinoxalinone imidazoles under microwave irradiation |
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Authors: | Suman Thummanagoti Chih-Hau Chen Zhan-Hui Xu Chung-Ming Sun |
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Institution: | (1) Department of Applied Chemistry, Laboratory of Combinatorial Drug Discovery, National Chiao Tung University, Hsinchu, 300-10, Taiwan; |
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Abstract: | Traceless synthesis of 2-aminoimidazoquinoxalinones has been performed on soluble polymer support under open-vessel microwave
dielectric heating. The reaction progression is monitored directly by the conventional proton NMR which indicated no release
of the substrate from the support. Fmoc-deprotected amino acid polymer conjugates react with 1,5-difluoro-2,4-dinitro benzene
to yield polymer bound dinitro fluoro amines, which are further substituted by various primary amines to yield PEG-immobilized
dinitrodiamines. Simultaneous reduction of aromatic meta-dinitro group leads to the traceless release of 2-quinoxalinones, followed by N-hetero cyclization with various isothiocyanates
in the presence of mercury(II)chloride to furnish 2-aminoimidazoquinolinone rings with three points of diversity at rapid
pace. |
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