Synthesis of 2-Methylsulfanyl-5,5-dimethyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5]azepin-8-one and 2,2-[(Ethane-1,2-diyl)- bis(sulfanediyl)]bis{5,5-dimethyl-5,6,7,8-tetrahydro-4H-thiazolo[5,4-c]azepin-8-one}

摘要

Proceeding with our studies in the field of thiazo-loazepine chemistry, we have prepared 2-thioxo-thiazoloketone I and 2-thioxothiazoloazepinone II by heating of 2-chlorothiazoloketone III or 2-chlorothia-zoloazepinone IV with thiourea and then with alkaline aqueous solution. Compounds I, II react with methyl tosylate in acetonitrile in the presence of potassium carbonate to form methyl derivatives V, VI, respectively (Scheme 1). Heating of 2-thioxothiazoloketone I with ethylene glycol ditosylate in the presence of potassium carbonate in acetonitrile yields compound VII, while 2-thioxothiazoloazepinone II forms compound VIII. Products VI, VIII were also prepared by the Schmidt reaction from compounds V, VII, respectively, under the conditions we described previously in yields of about 20%.