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3-Acylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium Salts and Their Transformation into 4-Aminoquinolinium-3-thiolates and Azaphenothiazine Derivatives

Zięba A.

Polish Journal of Chemistry

2008

Vol. 82, nr 7

1399-1399

3-Acylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium methyl sulfates 3 were obtained via acylation of 1-methyl-3-sulfanyl-1H-quinoline-4-thione (1) in the presence of a base and subsequent alkylation with dimethyl sulfate. Reactions of 3-acylsulfanyl-1-methyl- 4-methylsulfanyl-quinolinium chlorides 4 with primary aliphatic and aromatic amines led to 4-amino-1-methylquinolinium-3-thiolates (5). When the reactions of chlorides 4 with aniline were carried out in the presence of atmospheric oxygen, the 3-thiolate 5 formed in the first step of the reaction under went cyclization to 5-methyl-12H-quino-[3,4-b][1,4]benzo thiazinium chloride (6).