Functionalization of thiazoles. Selectivity in the reactions of 2-(dimethylamino)-1, 3-thiazoles with electrophiles: formation of Michael-type adducts and thiazolium salts

…, P Pedrini, C Venturoli, A Dondoni

Index: Medici, Alessandro; Pedrini, Paola; Venturoli, Clara; Dondoni, Alessandro Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2790 - 2793

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Citation Number: 16

Abstract

diethyl azodicarboxylate (DAZO), hyl isocyanate (TOSI), and chlorocyanoketene (CCK) in various solvents at room temperature gave the corresponding 1: l Michael-type adducts 2-4 in high yields (Scheme I). The rates of formation of these adducts were highly solvent dependent and fast in polar media. For instance, the reaction between DAZO and la to give 2 in acetonitrile at room temperature was completed after 24 h, whereas in diethyl ether 14 ...