Reactive Troponoids and <i>o</i>-Aminophenol. II. The Formation of Cyclohepta[<i>b</i>][1,4]benzoxazine and 11<i>H</i>-Cyclohepta[<i>b</i>][1,4]benzoxazin-10-one Derivatives from Isomeric Isopropyl-2-chlorotropones

Abstract

Abstract The reactions of three isomeric isopropyl-2-chlorotropones with o-aminophenol were investigated. 8-Isopropylcyclohepta[b][1,4]benzoxazine was obtained from 5-isopropyl-2-chlorotropone, while 4- and 6-isopropylderivatives gave the same mixture of 7- and 9-isopropylcyclohepta[b][1,4]benzoxazine. These facts showed that the amino group of o-aminophenol attacked both the C-1 and C-2 positions of 2-chlorotropones. Also 6-, 7-, and 8-isopropyl-11H-cyclohepta[b][1,4]benzoxazin-10-ones were obtained as the minor products of these reactions.