Abstract
Abstract 3-Acetyltropolone (1) and 2-acetyl-7-methoxytropone (2a) reacted with o-aminophenol in ethanol to afford 2-acetyl-7-(o-hydroxyanilino)tropone (3). The reaction of 3-acetyl-2-methoxytropone (2b) gave 3-acetyl-2-(o-hydroxyanilino)tropone (5). The compounds 3 and 5 were cyclized to 6-acetyl- and 10-acetylcyclohepta[b][1,4]benzoxazines (4 and 6), respectively, by heating their acetic acid solutions in the presence of a trace amount of concentrated sulfuric acid. The compounds 4 and 6 were also obtained directly from 1 (or 2a) and 2b, respectively, by the reaction with o-aminophenol in acetic acid. The compound 5 exists as a tautomeric mixture with 5′.
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