Studies on Heterocyclic Compounds. XL : Synthesis of 5, 8-Quinolinequinone Derivatives. (1). Reactions of 6-Methyl-5, 8-quinolinequinone with Amines

Abstract

As a part of systematic studies on 5, 8-quinolinequinone derivatives, reaction of 6-methyl-5, 8-quinolinequinone (I) with primary and cyclic secondary amines was carried out. The reaction of I with aziridine in benzene afforded 7-aziridino-6-methyl-5, 8-quinolinequinone (II) and that of I with hexamethyleneimine, piperidine, or pyrrolidine afforded-6-(substituted aminomethyl)-5, 8-dihydroxyquinolines (III-V). Reactions of I with primary amines (p-toluidine, p-anisidine, aniline, and cyclohexylamine) afforded 8-(N-substituted amino)-6-(N-substituted amino) methylidenequinolin-5-ones (VI, VIII-X).