Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction

Tetrahedron Lett. 2021 Apr 13:69:152951. doi: 10.1016/j.tetlet.2021.152951. Epub 2021 Feb 23.


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.