Bazı aktif karbonil bileşiklerinin pirazol-3-karboksilik asit türevleri ile kenetlenme reaksiyonlarının araştırılması ve yapılarının aydınlatılması

Abstract

Pirazol karboksilik asit türevleri antipretik, analjezik ve anti-inflamatuar özellikleri sebebiyle önemli heterosiklik bileşiklerdir. Yaptığımız bu çalışmada, pirazol-3-karboksilik asit ile bazı aktif karbonil bileşiklerinin kenetlenme reaksiyonu sonucu 3-8 bileşikleri elde edildi. Bu asitin 5-amino-1,3,4-tiyadiazol-2-sülfonamid ile reaksiyonu sonucu oluşan amit bileşiğinin de bazı aktif karbonil bileşikleriyle kenetlenme reaksiyonları sonucu 9-14 bileşikleri elde edildi.Sentezlenen bütün bileşiklerin yapıları spektral yöntemlerle aydınlatılmış olup, isimleri aşağıda verilmiştir;1-{3-[N'-(1-Asetil-2-oxo-propiliden)-hidrazin]-fenil}-4-benzoil-5-fenil-1H-pirazol-3-karboksilik asit , 4-Benzoil-1-{3-[N'-(1-benzoil-2-oxo-propiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit, 4-Benzoil-1-{3-[N'-(1-tert-bütoksikarbonil -2-oxo-propiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit, 4-Benzoil -1-{3-[N'-(1-etoksikarbonil -2-oxo-2-fenil-etiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit, 4-Benzoil-1-{3-[N'-(1-etoksikarbonil-2-oxo-propiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-(3-((2,4-dioxopentan-3-il)diazenil)fenil)-5-fenil-N-(5-sulfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamit , 4-Benzoil-1-{3-[N'-(1-benzoil-2-oxo-2-fenil-etiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit (5-sulfamoil-[1,3,4]tiyadiazol-2-il)-amit, 2-{3-[4-Benzoil-5-fenil-3-(5-sulfamoil-[1,3,4]tiyadiazol-2-il-karbamoil)-pirazol-1-il]-fenilazo}-malonik asit dietil ester, 2-({3-[4-Benzoil-5-fenil-3-(5-sulfamoil-[1,3,4]tiyadiazol-2-ilkarbamoil)-pirazol-1-il]-fenil}-hidrazon)-3-oxo-3-fenil-propionik asit etil ester, 2-({3-[4-Benzoil-5-fenil-3-(5-sulfamoil-[1,3,4]tiyadiazol-2-ilkarbamoil)-pirazol-1-il]-fenil}-hidrazon)-3-oxo-bütirik asit tert-butil ester, 4-Benzoil-1-{3-[N'-(1-benzoil-2-oxo-propiliden)-hidrazin]-fenil}-5-fenil-1H-pirazol-3-karboksilik asit (5-sulfamoil-[1,3,4]tiyadiazol-2-il)-amit.Anahtar kelimeler: Kenetlenme, pirazol karboksilik asitler, 1,3,4-tiyadiazol-2-sülfonamid

Pyrazole carboxylic acids and derivates are important heterocyclic compounds because of properties of their antipyretic, analgesic and antienflamatory. In this study of 3-8 compounds is obtained the coupling products of casequently the reactions carboxylic acid with some active carbonyl compounds. The coupling products (9-14) with some active carbonyl compounds is obtained of amide compound the occur resulting reaction of pyrazole -3-carboxylic acid with 5-amino-1,3,4-thiadiazole-2-sulphonamide.The all of the compounds have been characterized by 1H-NMR, 13C-NMR, FT-IR and mass spectral techniques. This compounds name are given at below;1-{3-[N'-(1-Acetyl-2-oxo-propylidene)-hydrazino]-phenyl}-4-benzoyl-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-Benzoyl-1-{3-[N'-(1-benzoyl-2-oxo-propylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-Benzoyl-1-{3-[N'-(1-tert-butoxycarbonyl-2-oxo-propylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-Benzoyl-1-{3-[N'-(1-ethoxycarbonyl-2-oxo-2-phenyl-ethylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-Benzoyl-1-{3-[N'-(1-ethoxycarbonyl-2-oxo-propylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-((2,4-dioxopentan -3-yl)diazenyl)phenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-Benzoyl-1-{3-[N'-(1-benzoyl-2-oxo-2-phenyl-ethylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid (5-sulfamoyl-[1,3,4]thiadiazol-2-yl)-amide, 2-{3-[4-Benzoyl-5-phenyl-3-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-pyrazol-1-yl]-phenylazo}-malonic acid diethyl ester, 2-({3-[4-Benzoyl-5-phenyl-3-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-pyrazol-1-yl]-phenyl}-hydrazono)-3-oxo-3-phenyl-propionic acid ethyl ester(12), 2-({3-[4-Benzoyl-5-phenyl-3-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-pyrazol-1-yl]-phenyl}-hydrazono)-3-oxo-butyric acid tert-butyl ester, 4-Benzoyl-1-{3-[N'-(1-benzoyl-2-oxo-propylidene)-hydrazino]-phenyl}-5-phenyl-1H-pyrazole-3-carboxylic acid (5-sulfamoyl-[1,3,4]thiadiazol-2-yl)-amideKey words : Coupling, pyrazole carboxylic acids, 1,3,4-thiadiazole-2-sülfonamide