Bazı pirazol-3-karboksilli asit klorürlerinin çeşitli hidrazin ve amitlerle reaksiyonları
Reactions of some pyrazole-3 carboxylic acid chlorides with various hydrazines and amides
Yazar: AYŞE ÇAĞLAYAN
Danışman: DOÇ. DR. İLHAN ÖZER İLHAN
Erciyes Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2011
Konu: Kimya = Chemistry
Dizin: Heterosiklik sistemler = Heterocyclic systems ; Nükleofilik reaksiyon = Nucleophilic reaction

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 hidrazin ve amitlerle reaksiyonlarının 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 (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 hidrazinler ve amitlerle reaksiyonları yapılarak sırasıyla; 4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3.karboksilli asit-2,4-dinitrofenil hidrazit (AC1), 4-benzoil-1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-2,4-dinitrofenil hidrazit (AC2), 4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-p-nitrofenil hidrazit (AC3), 4-benzoil-1-[2,4-dinitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-2,5-diklorfenil hidrazit (AC4), 4-benzoil?1-[4-nitrofenil]-5-fenil-1H-pirazol-3-karboksilli asit-2,5-diklorfenil hidrazit (AC5), 2-(2,4-dinitrofenil)-3,4,6-trifenil-2,6-dihidropirazolo-[3,4-d]piridazin-7-on (AC6), 2-(4-nitrofenil)-3,4,6-trifenil-2,6-dihidropirazolo-[3,4-d]piridazin-7-on (AC7), 2-(2,4-dinitrofenil)-3,4difenil-6-(3-nitrofenil)-2,6-dihidropirazolo-[3,4-d]piridazin-7-on (AC8), N,4-dibenzoil-1-(2,4-dinitrofenil)-5-fenil-1H-pirazol-3-karboksamit (AC9), N,4-dibenzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksamit (AC10) ve N-asetil-4-benzoil-1-(4-nitrofenil)-5-fenil-1H-pirazol-3-karboksamit (AC11) 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, Hidrazin, Amit, 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 hydrazine and amides 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-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid 2,4-dinitro phenylhydrazide (AC1), 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid 2,4-dinitro phenylhydrazide (AC2), 4-benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid 4-nitrophenylhydrazide (AC3), 4-Benzoyl-1-[2,4-dinitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid 2,5-dicloro phenylhydrazide (AC4), 4-benzoyl-1-[4-nitrophenyl]-5-phenyl-1H-pyrazole-3-carboxylic acid 2,5-dicloro phenylhydrazide (AC5), 2-(2,4-dinitrophenyl)-3,4,6-triphenyl-2,6-dihydropyrazolo-[3,4-d]pyridazin-7-one (AC6), 2-(4-nitrophenyl)-3,4,6-triphenyl-2,6-dihydropyrazolo-[3,4-d]pyridazin-7-one (AC7), 2-(2,4-dinitrophenyl)-3-(3-nitrophenyl)-4,6-diphenyl-2,6-dihydropyrazolo-[3,4-d]pyridazin-7-one (AC8), N,4-dibenzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-karboxamide (AC9), N,4-dibenzoyl-1-(2,4-dinitrophenyl)-5-phenyl-1H-pyrazole-3-karboxamide (AC10) and N-acetyl-4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-karboxamide (AC11) were obtained from the reaction of (4) and (5) with the corresponding hydrazides and amides. 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, Hydrazine, Amid, Nucleophilic Addition Reactions.