Bazı pirazol-3-karboksilli asitlerin tiyonil klorür, çeşitli aminler ve alkollerle reaksiyonları
Reactions of some pyrazole-3 carboxylic acids with thionyl chloride, various amides and alcohols
Yazar: SEVGİ ZÜHAL
Danışman: DOÇ. DR. İLHAN ÖZER İLHAN
Erciyes Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2008
Konu: Kimya = Chemistry
Dizin: Amidler = Amides ; Esterler = Esters ; Nükleofilik katılma = Nucleophilic addition ; Pirazol türevleri = Pyrazole derivatives ; Tiyonil klorür = Thionyl chloride

Özet:
Bu çalışmada, 4-Benzoil-1-(2,4-dinitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit klorürü ve 4-Benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit klorürünün çeşitli aminler ve alkollerle reaksiyonları araştırılması amaçlanmıştır.Bu araştırma on bir yeni bileşiğin sentezi ile sonuçlanmıştır. Öncelikle 4-Benzoil-1-(2,4-dinitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit (2) daha sonra 4-Benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit (3) bileşikleri sentezlenmiştir. 4-Benzoil-1-(2,4-dinitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit klorürü (SZ1) ve 4-Benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit klorürü (4) bileşikleri (2) ve (3) bileşiklerinin SOCl2 ile reaksiyonundan elde edilmiştir. Ardından (SZ1) ve (4) bileşiklerinin çeşitli aminler ve alkollerle reaksiyonları yapılarak sırasıyla; 4-Benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-N-o-Tolil amidi (SZ2), 4-Benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-N-o-Tolil amidi (SZ3), 4-Benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-N-p-Tolil amidi (SZ4), 4-Benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-N-p-Tolil amidi (SZ5), N,N'-Bis(4-benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-il-karbonil)-1,2-fenilendiamin (SZ6), N,N'-Bis(4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-il-karbonil)-1,2-fenilendiamin (SZ7), Etil 4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilat (SZ8), Etil 4-benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilat (SZ9), Metil 4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilat (SZ10), Metil 4-benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilat (SZ11) bileşikleri sentez edilmiştir. Sentez edilen bileşiklerin yapıları Elementel Analiz, NMR ve IR spektroskopisi yardımıyla aydınlatılmıştır.Anahtar Kelimeler: Pirazol-3-karboksilli asit, Pirazol-3-karboksilli asit klorür, Alkol, Nükleofilik Katılma Reaksiyonları, Ester, Amit

Abstract:
In this study, the reactions of 4-Benzoyl-1-(2,4-dinitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid chloride and 4-Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid chloride with various amines and alcohols were investigated.The investigation resulted in the synthesis of 11 new compounds. First, the compound 4-Benzoyl-1-(2,4-dinitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (2), then 4- Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (3), were synthesized. 4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid chloride (SZ1) and 4-Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid chloride (4) were obtained from the reaction of (2) and (3) with thionyl chloride. The compounds of 4-Benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid-N-o-Tolil amid (SZ2), 4-Benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid-N-o-Tolil amid (SZ3), 4-Benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid?N-p-Tolil amid (SZ4), 4-Benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid-N-p-Tolil amid (SZ5), N,N?-Bis(4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-yl-carbonyl)-1,2-phenylenediamine (SZ6), N,N?-Bis(4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-yl-carbonyl)-1,2-phenylenediamine (SZ7), Ethyl 4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (SZ8), Ethyl 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (SZ9), Methyl 4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (SZ10), Methyl 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylate (SZ11),were obtained from the reaction of (SZ1) and (4) with the corresponding alcohols and amines.The structure of these newly synthesized compounds were confirmed by using IR, NMR spectra and Elemental Analyses.Keywords: Pyrazole-3-carboxylic acid, Pyrazole-3-carboxylic acid chloride, Alcohol, Nucleophilic Addition, Ester, Amide