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

• Autorzy: Zięba A.
• Języki publikacji: EN

Abstrakty

EN

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).

Słowa kluczowe

EN

nucleophilic aromatic substitutions; phenothiazine; azaphenothiazine; quinolinium thiolates; quinolinium salts

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2008
• Tom: Vol. 82, nr 7
• Strony: 1399--1399
• Opis fizyczny: –1402, Bibliogr. 8 poz., rys.

Twórcy

autor

Zięba A.

• Department of Organic Chemistry, The Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland,

Bibliografia

• 1. part CI in the series of Azinyl Sulfides.Part C: Maślankiewicz A., Maślankiewicz M.J. and Marciniec K., Magn. Reson. Chem., (2008) in press.
• 2. Maślankiewicz A. and Zięba A., Heterocycles, 34, 247 (1992).
• 3. Zięba A., Maślankiewicz A. and Suwińska K., Eur. J. Org. Chem., 2947 (2000).
• 4. Zięba A. and Suwińska K., Heterocycles, 68, 495 (2006).
• 5. Sainsbury M., Comprehensive Heterocyclic Chemistry, eds. Katritzky A. and Rees C.W., Pergamon Press, Oxford, 1989, vol. 3, p. 1037.
• 6. Reynolds J.E.C., (ed.), The Pharmacopeia, 29 ed., The Pharmaceutical Press, London, 1989, p. 765.
• 7. Delgado J.N. and Remers W. A., (eds.), Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 10 ed., Lippincott-Raven Publishers, Philadelphia, 1998, p. 450.
• 8. Maślankiewicz A., Zięba A. and Głowiak T, Rec. Trav. Chim. Pays-Bas, 115, 371 (1996).