Synthesis of Phenanthrooxazoles from 10-(Methoxyimino)phenantrene-9-one

Article abstract of DOI:10.1016/S0040-4020(01)87251-3

10-(Methoxyimino)phenanthren-9-one 3 easily reacts with the methyl substituted aromatics 4(a-d), as well as with α-bromo-p-xylene 6 and the α-substituted methyl derivatives 7(a-i), to afford in 5-64percent yield the corresponding 2-aryl substituted phenanthro<9,10-d>oxazoles 5(a-g), most probably via a free radical reaction sequence.In several cases the unsubstituted oxazole 12 is also obtained, while reaction of compound 3 with the N-methyl substituted amines 7g and 14(a,b) leads to the aminooxazoles 13 and 15(a,b) respectively.