Summary
4-Dimethylamino-5,6-dihydro-2H-thiopyran-2-thiones (1) were alkylated to N,N-dimethyl-6-methylthio-2H-thiopyran-4(3H)-iminiumiodides (2). Aminolysis of the latter with ammonia led to 6-dimethylamino-2H-thiopyran-4(3H)-iminiumiodides (3) which were hydrolyzed to 3-amino-N,N-dimethyl-2,4-pentadienthioamides (4). Ring closure with sulfur gave 3-aminothiophene-2-thioamides (5). The configurations of the pentadienthioamides (4) have been investigated by NOE experiments. The structures of the thiophene-2-thioamides (5) were established by means of two-dimensional NMR techniques.
Zusammenfassung
4-Dimethylamino-5,6-dihydro-2H-thiopyran-2-thione (1) wurden zu N,N-Dimethyl-6-methylthio-2H-thiopyran-4(3H)-iminiumiodiden(2) alkyliert. Die Umsetzung mit Ammoniak führte zur Bildung von 6-Dimethylamino-2H-thiopyran-4(3H)-iminiumiodiden (3). Diese wurden zu 3-Amino-N,N-dimethyl-2,4-pentadienthioamiden (4) hydrolysiert. Beim Erhitzen mit Schwefel erfolgte Cyclisierung zu 3-Aminothiophen-2-thiocarboxamiden (5). Die Konfiguration der Pentadienthioamide (4) wurde mit NOE-Messungen untersucht, die der Thiophen-2-thiocarboxamide (5) mit Hilfe zweidimensionaler NMR-Methoden aufgeklärt.
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References
Meltzer RI, Lewis AD, King JA (1955) J Am Chem Soc77: 4062
Bercot-Vatteroni M (1962) Ann Chim7: 303
Kakimoto S, Seydel J, Wempe E (1961) Tuberk-Forschunginst Borstel, Jahresber5: 240
Pappalardo G, Tornetta B, Condorelli P, Bernardini A (1967) Farmaco Ed Sci22(10): 808
Davies RV (Boots Co PLC) Eur Pat Appl EP 269,295 (1988)
Russo F, Santagati A, Santagati M, Caruso A, Leone MG, Felice A, Amico-Roxas M (1989) Eur J Med Chem24(1): 91
Shishoo CJ, Pathak US, Jain KS, Devani IT, Chhabria MT (1994) Indian J Chem Sect B: Org Chem Incl Med Chem33B(5): 436
Gewald K, Schaefer H, Bellmann P, Germany (East) DD 263,055 (1988)
Gewald K, Ute H (1992) Monatsh Chem123: 455 and references cited therein
Schweiger K (1980) Monatsh Chem111: 1175
Schweiger K (1983) Monatsh Chem114: 317
Schweiger K, Schubert-Zsilavecz M, Weis R, Belaj F (1992) Monatsh Chem123: 133
Auer H, Weis R, Schweiger K, Schubert-Zsilavecz M (1994) Monatsh Chem125: 571
Pfister-Guillouzo G, Lozac'h N (1963) Bull Soc Chim Fr 153
Nguyen Kim Son, Clesse F, Quiniou H, Lozac'h N (1966) Bull Soc Chim Fr11: 3466
Meslin J-C, Quiniou H (1971) CR Acad Sci Ser C273: 148
Nguyen Kim Son, Pinel R, Mollier Y (1974) Bull Soc Chim Fr (3–4): 471
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Auer, H., Weis, R. & Schweiger, K. Synthesis of 3-aminothiophene-2-thioamides. Monatsh Chem 127, 1027–1030 (1996). https://doi.org/10.1007/BF00807574
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DOI: https://doi.org/10.1007/BF00807574