4-etoksi karbonil-1-(3-nitrofenil)-5-fenil pirazol-3-karboksilik asitin sentezi ve reaksiyonları

Abstract

4-ETOKS KARBON L-1-(3-N TROFEN L)-5-FEN L P RAZOL-3-KARBOKS L KAS T N SENTEZ VE REAKS YONLARIHamdiye DURANKimya Bölümü, Yüksek Lisans Tezi, 2006Tez Danışmanı: Yrd. Doç. Dr. Rahmi KASIMOĞULLARIÖZETBu çalışmada 4-Etoksi Karbonil-1-(3-Nitrofenil)-5-Fenil Pirazol-3-Karboksilik Asit'in(1) çeşitli nükleofillerle olan reaksiyonları araştırılmıştır. Bunun için ilk olarak etil-4,5-diokso-2-fenil-4,5-dihidrofuran 3-karboksilat bileşiğinin 3-nitrofenil hidrazonla reaksiyonundan yüksekbir verimle 1 bileşiği sentezlendi.Diğer yandan 1 bileşiğinin tiyonil klorür ile reaksiyonundan etil-3-(klorokarbonil)-1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat(2) bileşiği, bu bileşiğinde muhtelif alkol, amin veürelerle reaksiyonlarından, ester, amit ve üreid türevleri (3 ,4, 5, 6, 7, 8, 9, 10, 11, 12, 13)sentezlendi. Ayrıca 13 bileşiğinin soğukta DMF içerisinde SOCI2 ile reaksiyonu sonucu birkarbonitril türevi olan 14 bileşiğinin sentezi gerçekleştirildi. 1 bileşiğinin yüksek sıcaklıktadekarboksilasyonuyla 15 bileşiği elde edildi. Sentezlenen bütün bu bileşiklerin yapıları spektralmetotlarla aydınlatılmış olup, isimleri aşağıdaki şekilde sıralanabilir.4-(etoksikarbonil)-1-(3-nitrofenil)-5-fenil pirazol-3-karboksilik asit, Etil 3-(klorokarbonil)-1-(3-nitrofenil-5-fenil pirazol-4-karboksilat, 4-etil 3-metil 1-(3-nitrofenil)-5-fenil pirazol-3,4-dikarboksilat, dietil 1-(3-nitrofenil)-5-fenil pirazol-3,4-dikarboksilat, 4-etil 3-propil 1-(3-nitrofenil)-5-fenil pirazol-3,4-dikarboksilat, 4-etil 3-izopiropil 1-(3-nitrofenil)-5-fenil pirazol-3,4-dikarboksilat, 4-etil 3-fenil 1-(3-nitrofenil)-5-fenil pirazol-3,4-dikarboksilat,etil 3-(karbomoilkarbomoil)-1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat, etil 1-(3-nitrofenil)-5-fenil-3-(fenilkarbomoilkarbomoil) pirazol-4-karboksilat, etil 1-(3-nitrofenil)-3-(4-nitrofenilkarbomoil)-5-fenil pirazol-4-karboksilat, etil 3-(naftil-2-karbomoil)-1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat, etil 1-(3-nitrofenil)-5-fenil-3-(fenilkarbomoil)pirazol-4-karboksilat,etil 3-karbomoil-1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat, etil 3-siyano-1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat, etil 1-(3-nitrofenil)-5-fenil pirazol-4-karboksilat.Anahtar kelimeler: 4-etoksikarbonil-2-(3-nitrofenil)-5-fenil pirazol-3-karboksilik asit, pirazol,piridazin, nükleofilik katılma.

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.