Reactions of O-Methyl o-Quinone Monoximes with Methyl-, Methylene- and Methine- Substituted Aromatic Compounds. Synthesis of Benzo[d]oxazole and 1,4-Benzoxazine derivatives

Article abstract of DOI:10.1002/jhet.5570340602

O-MethyI o-quinone monoxime 1 reacts thermally with compounds 2a-d or 6a,b or 7a,b to give mainly the corresponding 2-substituted phenanthroxazoles 3a-c and 8. The reaction of 1 with aromatic methylene compounds 10a-c affords the ketones 13a-c in moderate to high yields. Similar products are also obtained from the reaction of monoximes 15a,b with some of the above reactants. The unexpected products 5 and 20 are obtained from the reaction of 1 with 2-methylimidazole (2d) and with phenyloxirane (19) respectively, while the 4H-1,4-oxazine derivative 23 is obtained from the reaction of 1 with indene (21).