Bazı pirazol-3-karboksilli asitlerin klorürlerin çeşitli hidrazitlerle reaksiyonları
Reactions of some pyrazole-3 carboxylic acids, various hydrazides
Yazar: MEHMET ÇADIR
Danışman: DOÇ. DR. İLHAN ÖZER İLHAN
Erciyes Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2011
Konu: Kimya = Chemistry
Dizin: Nükleofilik katılma = Nucleophilic addition

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 hidrazitlerle reaksiyonlarının araştırılması amaçlanmıştır.Bu araştırma onbir 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 (4) ve 4-Benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit klorürü (5) bileşikleri (2) ve (3) bileşiklerinin SOCl2 ile reaksiyonundan elde edilmiştir. Ardından (4) ve (5) bileşiklerinin çeşitli hidrazitlerle reaksiyonları yapılarak sırasıyla; 4-Benzoil-5-fenil-1-(2,4-dinitrofenil)-N'-benzoil-1H-pirazol-3-karbohidrazit (MC1), 4-Benzoil-5-fenil-1-(2,4-dinitrofenil)-N'-fenilasetil-1H-pirazol-3-karbohidrazit (MC2), 4-Benzoil-5-fenil-1-(2,4-dinitrofenil)-N'-(4-nitrobenzoil)-1H-pirazol-3-karbohidrazit (MC3), 4-Benzoil-5-fenil-1-(2,4-dinitrofenil)-N'-(2-nitrobenzoil)-1H-pirazol-3-karbohidrazit (MC4), 4-Benzoil-5-fenil-1-(2,4-dinitrofenil)-N'-asetil-1H-pirazol-3-karbohidrazit (MC5), 4-Benzoil-5-fenil-1-(4-nitrofenil)-N'-benzoil-1H-pirazol-3-karbohidrazit (MC7), 4-Benzoil-5-fenil-1-(4-nitrofenil)-N'-fenilasetil-1H-pirazol-3-karbohidrazit (MC8), 4-Benzoil-5-fenil-1-(4-nitrofenil)-N'-2-nitrobenzoil-1H-pirazol-3-karbohidrazit (MC9), 4-Benzoil-5-fenil-1-(4-nitrofenil)-N'-4-nitrobenzoil-1H-pirazol-3-karbohidrazit (MC10), 4-Benzoil-5-fenil-1-(4-nitrofenil)-N'-asetil-1H-pirazol-3-karbohidrazit (MC11) bileşikleri ve bunun yanında 4-Benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksilli asit (3) bileşiğinin dekarboksilasyonu ile [1-(4-nitrofenil)-5-fenil-1H-pirazol-4-il] fenilmetanon (MC12) bileşiği 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, Hidrazit, Nükleofilik Katılma Reaksiyonları

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 hydrazid 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 (4) and 4-Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid chloride (5) were obtained from the reaction of (2) and (3) with thionyl chloride. The compounds of 4-Benzoyl-5-phenyl-1-[2,4-dinitrophenyl]-N?-benzoyl-1H-pyrazole-3-carbohydrazide (MC1), 4-Benzoyl-5-phenyl-1-[2,4-dinitrophenyl]-N?-phenylacetyl-1H-pyrazole-3-carbohydrazide (MC2), 4-Benzoyl-5-phenyl-1-[2,4-dinitrophenyl]-N?-(4-nitrobenzoyl)-1H-pyrazole-3-carbohydrazide (MC3), 4-Benzoyl-5-phenyl-1-[2,4-dinitrophenyl]-N?-(2-nitrobenzoyl)-1H-pyrazole-3-carbohydrazide (MC4), 4-Benzoyl-5-phenyl-1-[2,4-dinitrophenyl]-N?-acetly-1H-pyrazole-3-carbohydrazide (MC5), 4-Benzoyl-5-phenyl-1-[4-nitrophenyl]-N?-benzoyl-1H-pyrazole-3-carbohydrazide (MC7), 4-Benzoyl-5-phenyl-1-[4-nitrophenyl]-N?-phenylacetyl-1H-pyrazole-3-carbohydrazide (MC8), 4-Benzoyl-5-phenyl-1-[4-nitrophenyl]-N?-(2-nitrobenzoyl)-1H-pyrazole-3-carbohydrazide (MC9), 4-Benzoyl-5-phenyl-1-[4-nitrophenyl]-N?-(4-nitrobenzoyl)-1H-pyrazole-3-carbohydrazide (MC10), 4-Benzoyl-5-phenyl-1-[4-nitrophenyl]-N?-acetyl-1H-pyrazole-3-carbohydrazide (MC11), were obtained from the reaction of (4) and (5) with the corresponding hydrazides and Besides [1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-4-ly] phenylmetanon (MC12) compound were synthesized with decarboxylation compound of 4- Benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid (3). 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, Hydrazide, Nucleophilic Addition