Synthesis and Reactions of New Thiazoles and Pyrimidines Containing Sulfonate Moiety

Treatment of 2-tosyloxybenzylidinethiosemicarbazone (2) with active halo compounds afforded thiazoles 3-5. Moreover, reaction of compound 2 with acetic anhydride or dimethylformamide dimethylacetal gave N, N diacetyl 6 and dimethylamino derivatives 7, respectively. Cyclization of thiazole derivatives 3 with some arylidenemalononitriles yielded thiazolo[2,3-d]pyrans 8-12. Multicomponent reaction of 2-tosyloxybenzaldehyde (1) with urea, thiourea, or compound 2 and ethyl acetoacetate or acetylacetone afforded pyrimidines 13-14. The structures of compounds were elucidated by elemental and spectral analyses.