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Treatment of the 1,3,4-oxadiazoles 3a and 3b with 3-chloropentane-2,4-dione gave the thiazoles 4a and 4b, respectively, which were methylated to furnish compounds 5a and 5b. The formation of 1,3,4-oxadiazoles using the 1,3-dithietane 1 as starting material, and the consecutive reactions mentioned above were transferred into sugar chemistry to provide the corresponding derivatives 6 - 9 in good yields. The reaction of 5a with benzyl amine, ethylene diamine and o-phenylene diamine afforded compounds 10, 11, and 12, respectively, which possess better stabilized push-pull systems than 5a. The structures of 3a, 4a, 5a, 10, 11, and 12 were compared with the previously proposed structures I - VI, respectively. The structures of compounds 1, 3b, and 11 were confirmed by X-ray diffraction studies.

Reinvestigation of the Thiazole Synthesis with Ethyl 3-Amino-2- [5-aryl-1,3,4-oxadiazol-2(3H)-ylidene]-3-thioxopropanoates and Related Reactions