Synthesis of new molecules from hydroxyl amine to Diels-Alder addition

Chalcones (flavonoids) are aromatic pigment compounds that have an antioxidant effect on fruits, vegetables and various beneficial biochemistry, acting as chemical messengers as physiological regulators or inhibitors of the cell cycle. The development of MAO-B (monoamine oxidases B isoform) inhibitor compounds in various chemical structures (pyrazoline, oxadiazole, coumarin, xanthine, chalcone, etc.), structure-activity relationships and neurodegenerative diseases have attracted attention in recent years. In the light of all this information, starting from the obtaining of 4- (benzyloxy) benzaldehyde (1) in the presence of 4-hydroxybenzaldehyde and benzyl chloride DMF, SOCl2 and ethanol were added to this molecule and synthesis of the molecule (E)-3-(4-(benzyloxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (2) was performed. The molecule number 2 (1Z, 2E) -3- (4- (benzyloxy) phenyl) -1- (4-hydroxyphenyl) prop-2-en-1-one oxime (3) molecule was synthesized using hydroxylamine hydrochloride reagent. As a result of ring closure using 3 molecule DDQ reagent, 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenol (4) was obtained. In the following reaction, 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenyl acetate (5) molecule was obtained by the acetate reaction. Finally, the molecule number 4 was treated with acryloyl chloride and triethylamine reagent and 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenyl acrylate (6) was obtained by the Diels-Alder addition method of double bonds and the new molecule was synthesized. .The sensor property was examined for the last molecule obtained. Sensory properties against all metals were examined and the molecule that was "turn off" (6) was treated with amino acid (cysteine) and turned on. The synthesized molecules were characterized using 1H NMR, 13C NMR and FT-IR spectroscopic data.