REACTIONS OF O-METHYL O-QUINONE MONOOXIMES WITH METHYL-SUBSTITUTED, METHYLENE-SUBSTITUTED AND METHINE-SUBSTITUTED AROMATIC-COMPOUNDS - SYNTHESIS OF BENZO[D]OXAZOLE AND 1,4-BENZOXAZINE DERIVATIVES
Dn. Nicolaides et al., REACTIONS OF O-METHYL O-QUINONE MONOOXIMES WITH METHYL-SUBSTITUTED, METHYLENE-SUBSTITUTED AND METHINE-SUBSTITUTED AROMATIC-COMPOUNDS - SYNTHESIS OF BENZO[D]OXAZOLE AND 1,4-BENZOXAZINE DERIVATIVES, Journal of heterocyclic chemistry, 34(6), 1997, pp. 1651-1656
O-Methyl o-quinone monoxime 1 reacts thermally with compounds 2a-d or
6a,b or 7a,b to give mainly the corresponding 2-substituted phenanthro
xazoles 3a-c and 8. The reaction of 1 with aromatic methylene compound
s 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 s
ome of the above reactants. The unexpected products 5 and 20 are obtai
ned from the reaction of 1 with 2-methylimidazole (2d) and with phenyl
oxirane (19) respectively, while the 4H-1,4-oxazine derivative 23 is o
btained from the reaction of 1 with indene (21).