In Situ Generation of Nitroso Compounds from Catalytic Hydrogen Peroxide Oxidation of Primary Aromatic Amines and Their One‐Pot Use in Hetero‐Diels–Alder Reactions

A method for in situ generation of nitroso compounds from organoselenium‐catalyzed oxidation of anilines by hydrogen peroxide was developed. The generated nitroso compounds were subsequently used in hetero‐Diels–Alder reactions. A variety of oxazines were synthesized in reasonable to good yields by this one‐pot procedure using primary aromatic amines with different substituents and various conjugated dienes. This strategy might facilitate the current methodologies for nitroso chemistry since no isolation or purification of the nitroso compounds is required. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)