Cyclocondensation of 1-Tosyl-2,2-dichloroethyl Isothiocyanate with O-, S-, N-, and C-Nucleophiles

摘要

Treatment of 1-tosyl-2,2-dichloroethenyl isothiocyanate with alcohols, thiols, primary and secondary amines, hydrazine and its derivatives, and phosphonium ylides results in addition of the O-, S-, N-, or C-nucleophilic center to the isothiocyanate group, followed by cyclocondensation with elimination of hydrogen chloride and formation of the corresponding 2-functionally substituted 4-tosyl-5-chloro-1,3-thiazoles. Further transformations of these compounds were studied, and a series of previously unknown types of 3-functionally substituted 1,3-thiazole derivatives were prepared.