4-benzoil-1-(3-aminofenil)-5-fenil-pirazol-3-karboksilli asitin bazı yeni türevlerinin sentezi ve yapılarının aydınlatılması

Abstract

Bu çalışmada, pirazol karboksilik asit ve türevlerinin çeşitli nükleofillerle yerdeğiştirme ve kenetlenme tepkimeleri araştırılmıştır. İlk olarak 1 ve 2 bileşiklerinin, diazonyum tuzlarının; su, iyot ve siyano nükleofilleriyle yerdeğiştirme reaksiyonları sonucu 4, 5, 6, 9, 10, 11 bileşikleri, fenol ve ß-naftol ile kenetlenme tepkimeleri sonucu 7, 8, 12, 13 bileşikleri elde edildi. Aynı yöntemle 3 bileşiğinin ß-naftol ile kenetlenme tepkimesi sonucu 14 bileşiği sentezlendi. 2 bileşiğinin, kloroaseton ile halkalanması sonucu, yeni bir indol bileşiği (15) elde edildi. Sentezlenen bütün bileşiklerin yapıları spektral metotlarla aydınlatılmış olup, isimleri aşağıda verilmiştir;4-benzoil-1-(3-hidroksi-fenil)-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-(3-iyado-fenil)-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-(3-siyano-fenil)-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-[3-(4-hidroksi-fenilazo)-fenil)]-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-[3-(2-hidroksi-naftalin-1-ilazo)-fenil]-5-fenil-1H-pirazol-3-karboksilik asit, 4-benzoil-1-(3-hidroksi-fenil)-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-(3-iyodo-fenil)-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-(3-siyano-fenil)-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-[3-(4-hidroksi-fenilazo)-fenil)]-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-[3-(2-hidroksi-naftalin-1-ilazo)-fenil]-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid, 4-benzoil-1-[3-(2-hidroksi-naftalin-1-ilazo)-fenil]-5-fenil-1H-pirazol-3-karboksilikasit fenilamid, 4-benzoil-1-(2-metil-1-(2-oksopropil)-1H-indol-4-il)-5-fenil-N-(5-sülfamoil-1,3,4-tiyadiazol-2-il)-1H-pirazol-3-karboksamid.Anahtar kelimeler: Diazolama, kenetlenme, pirazol karboksilik asitler, yerdeğiştirme.

In this study are investigated the substitution and coupling reactions of pyrazole carboxlic acid and its derivatives with various nucleophiles. The first 4,5,6,9,10,11 compounds synthesized the resulting substitution reactions with water, iodine and cyno nuceophiles the prepared diazonium salts of 1 and 2 compounds. 7,8,12,13 compunds are obtained resulting coupling rections with phenole and ß-naphtole of 1 and 2 compounds. The compound of 14 is synthesized the resulting coupling rection to the compound of 3 with ß-naphtole the used same methods. A novel compound of indole 15 is produced of consequently the csclization compound of 2 with chloroacetone. 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;4-benzoyl-1-(3-hydroxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-iodophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-cyanophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-((4-hydroxyphenyl)diazenyl)phenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-((2-hydroxynaphthalen-1-yl)diazenyl) phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid, 4-benzoyl-1-(3-hydroxyphenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(3-iodophenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(3-cyanophenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(3-((4-hydroxyphenyl)diazenyl)phenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(3-((2-hydroxynaphthalen-1-yl)diazenyl)phenyl)-N,5-diphenyl-1H-pyrazole-3-carboxamide, 4-benzoyl-1-(2-methyl-1-(2-oxopropyl)-1H-indol-4-yl)-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide.Key words : Diazonium salt, coupling, pyrazole carboxylic acids, substitution.