The synthesis and reactions of 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl pyrazole-3-carboxylic acid

THE SYNTHESIS AND REACTIONS OF 4-( ETHOXYCARBONYL)-1-( 3 -N TROPHENYL)-5-PHENYL PYRAZOLE-3-CARBOXYL C AC DHamdiye DURANChemistry Department, M.S. Thesis, 2006Thesis Supervisor: Yard. Doç. Rahmi KASIMOĞULLARISUMMARYIn this study, the reactions of 4- ( ethoxycarbonyl) -1- ( 3- nitrophenyl pyrazole -3-carboxylic acid (1) with various nükleofils. (1) compound, yield of was efficiently synthesiedfrom the reaction of ethyl 4,5-dioxo -2- fenil-4,5-dihidrofuran -3- carboksilat with 3-nitrofenil hydrazon. Besides, ethyl 3-(chlorocarbonyl) -1-(3-nitrophenyl) -5- phenyl pyrazole -4-carboxylate (2) compound was synthesized.The deriatives of amide, ester, amine and üreid were obtaired from the reaction of thiscompound with alchol, amine and üre (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13) the 14 compound wasabtained from the reaction of 13 with DMF in SOCl2 solution at low temperature. 15 compoundwas synthesied from the decarboxcilation reaction of 1 at ambient temperature. The structuresof all these compounds, which were synthesized, were illuminated by means of spectralmethods. Their names can be enumerated like this.4- ethyl 3- methyl 1-(3-nitrophenl)-5-phenyl pyrazole-3,4-dicarboxylate, diethyl 1-(3-nitrophenyl)-5-phenyl pyrazole-3,4-dicarboxylate, 4-ethyl 3-propyl 1-(3-nitrophenyl) -5- phenylpyrazole -3,4-dicarboxylate, 4-ethyl 3-isopropyl 1-(3-nitrophenyl)-5-phenyl pyrazole -3,4-dicarboxylate, 4-ethyl 3-phenyl 1-(3-nitrophenyl)-5-phenyl pyrazole -3,4-dicarboxylate, ethyl 3-(carbamoylcarbamoly)-1-(3-nitrophenyl)-5-phenyl pyrazole-4-carboxylate, ethyl 1-(3-nitrophenyl)-5-phenyl-3-(phenylcarbamoylcarbamoyl) pyrazole-4-carboxlate, ethy 1-(3-nitrophenyl) -3-(4-nitrophenylcarbomoyl)-5-phenyl pyrazole-4-carboxylate, ethyl 3-(naphthalen-2-ylcarbamoyl)-1-(3-nitrophenyl)-5-phenyl pyrazole-4-carboxylate, ethyl 1-(3-nitrophenyl)-5-phenyl-3-(phenylcarbamoyl) pyrazole-4-carboxylate, ethyl 3-carbamoyl-1-(3-nitrophenyl)-5phenyl pyrazole-4-carboxylate, ethyl 3-cyano-1-(3-nitrophenyl)-5-phenyl pyrazole-4-carboxylate, ethyl 1-(3- nitrophenyl)-5-phenyl pyrazole -4- carboxylate.Key words : 4-(ethoxycarbonyl)-1-(3-nitrophenyl)-5-phenyl pyrazole-3-carboxylic acid,cylooddition, nucleophilic addition.