Davis–Beirut reaction inspired nitroso Diels–Alder reaction
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Elsevier Ltd
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. © 2021 Elsevier Ltd
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Keywords
1,2-oxazines, Davis-beirut reaction, Nitroso diels-alder, Nitrosobenzene, One-pot protocol, 1,2 oxazine derivative, Alcohol, Amine, Benzene derivative, Dihydro 1,2 oxazine derivative, Nitrophenyl, Nitroso derivative, Unclassified drug, Article, Chemical modification, Chemical reaction, Davis beirut reaction, Deprotonation, Diels alder reaction, One pot synthesis, Oxidation, Physical chemistry, Reduction (chemistry)