Bulletin of the Chemical Society of Japan p. 3337 - 3338 (1982)
Update date:2022-09-26
Topics:
Imafuku, Kimiaki
Shigenobu, Akihiro
Ogura, Makoto
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<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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(1983)
