Synthesis of some acridines and 9-acridones for spectral studies

Abstract

A series of alkyl-substituted 9-chloroacridines and 9-acridones have been synthesised from N-arylanthranilic acids; the n.m.r. spectra of the chloroacridines and the i.r. and u.v. spectra of the 9-acridones have been investigated. 2-Cyclohexyloxybenzoic acid was formed from 2-chlorobenzoic acid and the cyclohexanol used as solvent in some Ullmann reactions. Petrow's mechanism for the conversion of 2-anilinomethylenecyclohexanones into tetrahydroacridines has been confirmed. A steric effect is displayed in the homolytic α-bromination of 2- and 4-alkyl-9-chloroacridines.