Synthesis of some acridines and 9-acridones for spectral studies

Authors:
  • RAR. Morrin Acheson
    R. Morrin Acheson
  • RBRoger G. Bolton
    Roger G. Bolton
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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.