Synthesen von N-substituterten o-Methylthioanilinderivaten

Zusammenfassung

Methylierung von o-Aminothiophenol lieferte o-Methylmercapto-anilin, dessen Tosylat zur Herstellung des Tosylates der N-(o-Methylmercaptophenyl)-β-aminopropionsäure verwendet wurde. Cyclisierung von β-(2′-Methylmercaptodiphenyl)-aminopropionsäure ergab 1-(2′-Methylmercaptophenyl)-4-oxo-1,2,3,4-tetrahydrochinolin, dessen Oxim zu 1-(2′-Methylmercaptophenyl)-4-amino-1,2,3,4-tetrahydrochinolin reduziert wurde. N-[γ-(4′-Methylpiperazinyl-1′)-propyl]-2-methylthiodiphenylamin wurde durch Direktsubstitution van 2-Methylthio-diphenylamin erhalten.

Abstract

Methylation of o-aminothiophenol gave o-methyl-mercaptoaniline, the tosylate of which was used for the preparation of N-(o-methylmercaptophenyl)-β-aminopropionic acid tosylate. Cyclization of β-(2′-methylmercapto-diphenyl)-aminopropionic acid yielded 1-(2′-methylmercaptophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline, the oxime of which was reduced to 1-(2′-methylmercaptophenyl)-4-amino-1,2,3,4-tetrahydroquinoline. N-[γ-(4′-Methylpiperazino-1′)-propyl]-2-methylmercapto-diphenylamine was prepared by direct su stitution of 2-methylmercapto-diphenylamine.