Oldukça işlevselleştirilen tiyazolo[3,2-a]piridin-8-il-fosfonat türevlerinin tek basamakta sentezi

In this study, highly effecient synthesis of thiazolo[3,2-a]pyridin-8-yl-phosphonate containing heterocycles were succeeded via multicomponent reactions (MCRs) which proceeds through a domino-Knoevenagel condensation/nucleophlic addition/ condensation sequence to afford titled products. Moreover, the mechanism of formation leading to the obtained product was anticipated. As the major course of this study, our starting material diethyl phosphonate containing heterocyclic ketene aminal (HKA), diethyl ((4-oxothiazolidin-2-ylidene)methyl)phosphonate, was synthesized for the first time. Then, it was reacted with malononitrile and two equivalents of various aromatic aldehydes to give thiazolo[3,2-a]pyridin-8-yl-phosphonate derivatives. Precipitated products were filtered and purified by recrystallization with good to excellent yields. All compounds were screened for anticancer properties against mcf7 and t98g cancer cells. Diethyl-(Z)-(5-amino-6-cyano-2-(4-nitrobenzylidene)-7-(4-nitrophenyl)-3-oxo-3,7-dihydro-2H-thiazolo[3,2-a]pyridin-8-yl)phosphonate showed significant cytotoxic activity against breast cancer cell line. The structures of all multi-component reaction products were identified by means of spectroscopic methods IR, 1H NMR, 13C NMR, HRMS and physical characteristics (melting point and Rf values).