Investigations of Reactions of 2,3-Furandions

Abstract

Pirazol türevleri anti-mikrobial, anti-piretik, analjezik ve anti-inflammatuar özellikleri şeklinde ortaya çıkan biyolojik aktiviteleri sebebiyle son yıllarda dikkatleri üzerine çeken önemli heterosiklik bileşiklerdir. 4-benzoil-5-fenil-2,3-furandionlardan çıkılarak literatüre kazandırılmış birçok pirazol türevleri, zikredilen aktivitelerinden dolayı şimdiye kadar büyük oranda araştırmalara konu olmuşlardır.Bu çalışmada sırasıyla N-nükleofiller ve çeşitli karbonillerle yeni bisiklik oksalil bileşiği olan 4-benzoil-5-fenil-2,3-furandion ve 4-etoksikarbonil-5-fenil-2,3-furandionun nükleofilik ve siklokatılma reaksiyonları araştırıldı.Sonuç olarak 4-benzoil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karboksilik asit'in (SE-1), 4-benzoil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karbonil klorür`ün (SE-2), 4-benzoil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karboksilik asit metil esteri'nin (SE-3), 4-benzoil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karboksilik asit etil esteri'nin (SE-4), (1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-4-il)(fenil)metan-on'un (SE-5), 4-etoksikarbonil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3- karboksilik Asit'in (SY-1), 4-etoksikarbonil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3 karbonil klorür'ün (SY-2), 4-etoksikarbonil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3- karboksilik asit etil esteri'nin (SY-3), 4-etoksikarbonil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karboksiamid'inin (SY-5), 4-etoksikarbonil-1-(3,4-dimetilfenil)-5-fenil-1H-pirazol-3-karboksilik asit N-etilamid'inin (SY-6) sentezi gerçekleştirildi.Bu bileşiklerin yapıları elementel analiz, IR, 1H-NMR ve 13C-NMR spektrumları ile aydınlatılmıştır.Anahtar Kelimeler: 4-benzoil-5-fenil-2,3-furandion, 4-etoksikarbonil-5-fenil-2,3-furandion, pirazol, nükleofilik katılma

In last years, pyrazole derivatives which have some biological features like antimicrobial, anti-piratic, analjesic and anti-inflammatory are important heterocyclic compounds which scientists have focused on. Thus, far many pyrazole derivatives which have been yielded by using 4-bezoyl-5-phenyl-2,3-furandiones have been a topic for resarching because of their biological activities.In this study, 4-bezoyl-5-phenyl-2,3-furandione and 4-ethoxycarbonyl-5-phenyl-2,3-furandione?s which is a new bicyclic compound of N-nucleophiles and various carbonyl oksalil, nucleophilic and cycloaddition reactions waere investigated.As a result, synthesis of 4-benzoyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid?s (SE-1), 4-benzoyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3-carbonyl chloride?s (SE-2), methyl 4-benzoyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3-carboxylate?s (SE-3), ethyl 4-benzoyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3-carboxylate?s (SE-4), (1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-4-il)(phenyl)methanone?s (SE-5), 4-ethoxycarbonyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3- carboxylic acid?s (SY-1), 4-ethoxycarbonyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3 carbonyl chloride?s (SY-2), ethyl 4-ethoxicarbonyl-1-(3,4-dimethylphenyl)-5-phenyl-1H-pyrazole-3-carboxylate?s (SY-3), 4-ethoxycarbonyl-1-(3,4-dimetylphenyl)-5-phenyl-1H-pyrazole-3-carboxamide? (SY-5),4-ethoxycarbonyl-N-ethyl-1-(3,4-dimetylphenyl)-5-phenyl-1H-pyrazole-3 carboxamide?s (SY-6) were taken placed.The structures of these derivatives have been defined by elementel analysis, IR, 1HNMR and 13C-NMR.Key Words: 4-benzoyl-5-phenyl-2,3-furandione, 4-ethoxycarbonyl-5-phenyl-2,3-furandione, pyrazole, nucleophilic addittion?