4-benzoil-1,5-difenil-1H-pirazol-3-karboksilik asit klorünün bazı ambident nükleofillerle reaksiyonları
Reactions of 4-benzoyl-1,5-difenyl-1H-pyrazole-3- carboxylic acid chloride with various binuleophiles
Yazar: ELİF DEMİR
Danışman: PROF.DR. İSMAİL YILDIRIM
Erciyes Üniversitesi / Fen Bilimleri Enstitüsü / Kimya Ana Bilim Dalı
Derece: Yüksek Lisans, 2004
Konu: Kimya = Chemistry

Özet:
IV 4-BENZOIL-l,5-DIFENIL-lJÎ-PIRAZOL-3- KARBOKSİLİK ASİT KLORÜRÜNÜN BAZI AMBİDENT NÜKLEOFİLLERLE REAKSİYONLARI ÖZET Bu çalışmada, 4-benzoil-l,5-difenil-lfl-pirazol-3-karboksilli asit klorürünün çeşitli ambident nükleofillerle olan reaksiyonlan araştırılmıştır. Bu araştırma on iki yeni bileşiğin senteziyle sonuçlanmıştır. Öncelikle 4-benzoil-l,5- difenil-liJ-pirazol-3-karboksilik asit (2)'in SOCİ2 ile reaksiyonundan 4-Benzoil-l,5- difenil-lii/-pirazol-3-karboksilik asit klorürü (3) bileşiği sentezlenmiştir. Ardmdan 3 bileşiğinin çeşitli aromatik diaminlerle reaksiyonlan yapılarak sırasıyla; N,N'-bis(4- benzoil-l,5-difenil-l//-pirazol-341-karbonil)-l,2-fenilendiamin(4), N,N'-bis(4-benzoil- 1,5-difenil- liî-pirazol-3-il-karbonil)- 1,4-fenilendiamin (5), İV^V-bis(4-benzoil- 1,5- difeml-lff-pirazol-S-il-karboni^^-metil-ljl-fenilendiamin (6), JV,İV-bis(4-benzoil-l,5- difenil- lü/-pirazol-3-il-karbonil)-4,5-dimetil- 1,2-fenilendiamin (7), A^V-bis(4-benzoil- l,5-difeml-l/7-pirazol-341-karbonil)-4-klor-l,2-fenilendiamin (8), da A^İV-bis(4- benzoil-l,5-difenil-li/-pirazol-3-il-karbonil)-4-nitro-l,2-fenilendiamin (9), A^V-bis(4- benzoil- 1,5-difenil- lif-pirazol-3-il-karbonil)-2,3-diaminopiridin (1 0), 2-(4-benzoil- 1,5- difeml-liy-pirazol-3-il)-3/f-imidazo[4,5-ö]pMdm-l,4-diiyumdMorür (11), Ar^V-bis(4- benzoil-l,5-mTenil-li7-pkazol-3-il-karbonil)-l,2-propandiamin (12), NJf-bis(4- benzoil- 1,5-difenil- l#-pirazol-3-il-karbonil)- 1,2-etilendiamin (13), JVjS-bis^-benzoil- 1,5-difenil-l#-pnazol-3-il-karboml)-2-ammotiyofenol (14), 2- {[(4-benzoil-l,5-difenil- li/-pkazol-3-il)karbonil]amino}fenil 4-benzoil-l,5-difenil-li7-pirazol-3-karboksilat (15) bileşikleri sentez edilmiştir. Sentez edilen bileşiklerin yapılan elementel analiz, NMR ve İR spektroskopisi yardımıyla aydınlatılmıştır. Sonuçlar reaksiyonlarda kullanılan nükleofillerin ve sentez edilip kullanılan substratlann yapı ve özellikleri yönünden karşılaştınlmalı olarak tartışılmıştır. Anahtar Kelimeler: Pirazol-3-karboksilik asit klorür, Alifatik diamin, Aromatik diamin, Aminofenol.

Abstract:
REACTIONS OF 4-BENZOYL-l,5-DIPHENYL-lH-PYRAZOLE-3- CARBOXYLIC ACID CHLORIDE WITH VARIOUS BINUCLEOPHILES SUMMARY In this study, the reactions of 4-benzoyl-l,5-diphenyl~l//-pyrazole-3-carboxylic acid chloride with various aromatic and aliphatic diamines were investigated. The investigation resulted in the synthesis of 12 new compounds. First, the compound of 4-benzoyl-l,5~diphenyl-li/-pyrazole-3-carboxylic acid (2) was synthesized. Then of 4-benzoyl-l,5-diphenyl-l//-pyrazole-3-carboxylic acid chloride (3) was obtained from the reaction of 2 with thionyl chloride. JV,N'-bis(4-benzoyl-l,5-diphenyl-l//-pyrazol-3- y 1-carbonyl)- 1,2-phenylenediamine (4), NJf '-bis(4-benzoyl- 1,5 -diphenyl- 1 //-pyrazol- 3-yl-carbonyl)-l,4-phenylenediamine (5), iVy/V'-bis(4-benzoyl- 1,5 -diphenyl- 1 H- pyrazol-3-yl-carbonyl)-4-methyl-l,2-phenylenediamine (6), JV,N'-bis(4-benzoyl-l,5- diphenyl- 1 i/-pyrazol-3-yl-carbonyl)-4,5-dimethyl- 1,2-phenylenediamine (7), NJf '- bis(4-benzoyl-l,5-diphenyl-l//-pyrazol-3-yl-carbonyl)-4-chloro-l,2-phenylenediamine (8), NJN '-bis(4-benzoyl- 1,5 -diphenyl- 1 //-pyrazol-3 -yl-carbonyl)-4-nitro- 1,2- phenylenediamine (9), A^/V-bis(4-benzoyl-l,5-diphenyl-l//-pyrazol-3-yl-carbonyl)- 2,3-diaminopyridine (10), 2-(4-benzoyl-l,5-diphenyl-l//-pyrazol-3-yl)-3i/- imidazo[4,5-ö]pyridine-l,4-diiumdichloride (11), JV,JV'-bis(4-benzoyl-l,5-diphenyl-li/- pyrazol-3-yl-carbonyl)-l,2-propanediamine (12), JV,N'-bis(4-benzoyl-l,5-diphenyl-lif- pyrazol-3-yl-carbonyl)- 1,2-ethylenediamine (13), iV,5-bis(4-benzoyl- 1,5-diphenyl- 1 H- pyrazol-3 -yl-carbonyl)-2-aminothiophenol (14), 2- { [(4-benzoyl- 1,5-diphenyl- 1 H- pyrazol-3-yl)carbonyl]amino}phenyl 4-benzoyl-l,5-diphenyl-lif-pyrazol-3- carboxylate) (15) were obtained from the reaction of 3 with the corresponding some diamines and aminophenols. The structure of these synthesized new compounds were confirmed by using IR, NMR spectra and elemental analyse. The effects and the behavior of the nucleophiles and the new substrates in these reactions were discussed comparably according to their properties and structures. Key words: l/f-pyrazole-3-carboxylic acid chloride, Aliphatic diamine, Aromatic diamine Aminophenol.