Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction
Jung-Ho Son1, Amy Cheung1, Jie S Zhu1
1Department of Chemistry, University of California, Davis, One Shields Ave., Davis, CA 95616.
Abstract:
A Davis-Beirut reaction inspired nitroso Diels-Alder protocol is reported. The starting material for the procedure is a nitrophenyl moiety with the para position appropriately substituted with a 2°-amine (see 5) or 2°-alcohol (see 6). Deprotonation at the benzylic position followed by concomitant oxidation of the benzylic position and reduction of the nitro moiety delivers a nitrosophenyl intermediate, which subsequently undergoes a nitroso Diels-Alder reaction. This one-pot procedure delivers aryldihydro-1,2-oxazines in moderate yields.
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