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Quinones Quinones Q 0910Synthesis and Spectral Properties of N-Aryl-5-hydroxy-1,4-naphthoquinone 4-Imines. -A comparative study of oxidative amination of hydroxynaphthalenes (I), (IV), and (VII) with arylamines (II) and (V) by using three different oxidants is performed. The effect of electronic and steric factors in the arylamine on the yield and spectral properties of naphthoquinone imines (III), (VI), and (VIII) is examined. In the presence of K 3 Fe(CN) 6 , the yield of imines decreases from 85 to 3% in parallel with the basicity of arylamines. Generally, the reaction of hydroxynaphthalenes with arylamines in the presence of HIO 3 or NaIO 4 is characterized by higher yields of imines. The imine formation between tetrabromodihydroxynaphthalene (VII) and butoxyaniline (V) is accompanied by bromine replacement in position 2 through the arylamine residue yielding side product (IX). -(BUKHTOYAROVA, A. D.; EKTOVA, L. V.; ALEKSEEV, S. N.; BEREGOVAYA, I. V.; Russ.