Reactive Troponoids and o-Aminophenol. V. The Reaction of 3-Bromo-2-methoxytropone and o-Aminophenol

Article abstract of DOI:10.1246/bcsj.56.2756

The reaction products of the title substances in hot acetic acid were separated by preparative TLC into compounds A-L according to the R_f-values, and the structural assignments for these products were now made as follows: A, 14H-<1,4>benzoxazino<3',2':3,4>cyclohepta<1,2-b><1,4>benzoxazine; B, 1-formylphenoxazine; F, cyclohepta<2,1-b:2,3-b'>di<1,4>benzoxazine; G, cyclohepta<1,4>benzoxazin-10(11H)-one or its enolic form; J, cyclohepta<1,4>benzoxazin-6(11H)-one; L, 6-(o-hydroxyanilino)cyclohepta<1,4>benzoxazine hydrobromide. A small amount of 2-methylamino-3H-phenoxazin-3-one was also produced. Possible reaction pathways for the formation of these products are also discussed.