Journal
NEW JOURNAL OF CHEMISTRY
Volume 40, Issue 7, Pages 6389-6395Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5nj03707g
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A highly regio and diastereoselective copper catalyzed three component reaction of tetrahydroisoquinolines ( THIQs), aldehydes, and naphthols to furnish naphthoxazine derivatives under mild conditions was developed. The initial generation of iminium ions followed by the nucleophilic attack of naphthol presumed to deliver 15-phenyl-7a,12,13,15-tetrahydronaphtho[1',2':5,6][1,3]oxazino[2,3-a] isoquinoline derivatives. The reaction ensured the formation of C-C, C-N and C-O bonds in a one-pot reaction to produce ring fused N,O-acetals in good yields. The three component reaction, the inexpensive copper catalyst in the absence of a co-oxidant/additive and the direct regioselective oxidative sp(3) C-H functionalization are the attractive features of this approach. The preliminary photophysical properties obtained for selected compounds were presented.
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