Publication: Yeni benzokumarin türevi taç eterlerin sentezi ve yapılarının aydınlatılması
Abstract
Kumarin (2H-1-benzopiran-2-on) ve türevi olan bileşikler yararlı farmakolojik aktivite gösteren doğal bileşiklerin önemli bir sınıfını oluştururlar. Antikanserojenik, antifungal, antikoagulan ve etkin fluoresan verme gibi birçok özellikleri olan bu bileşiklerin ve taç eter türevlerinin sentezi ile ilgili olarak çok sayıda çalışma yapılmıştır. Yapılan bu çalışmada yeni benzokumarin türevi taç eterlerin sentezi gerçekleştirilmiş ve yapıları aydınlatılmıştır. 3-(3,4-Dimetoksifenil)kumarin ve 5,6-benzo-3-(3,4-dimetoksifenil)kumarin Perkin Reaksiyonu ile sentezlendi. Bu bileşikler demetilleme reaksiyonuna sokularak 3-(3,4-dihidroksifenil)kumarin ve 5,6-benzo-3-(3,4-dihidroksifenil)kumarin bileşikleri elde edildi. 5,6-benzo-3-(3,4-dihidroksifenil)kumarin etanolde kristallendirilerek saflaştırıldı ve asetonitril çözeltisinde polietilenglikolditosilatlarla reaksiyona sokularak yeni 4-,5-,6- oksijen atomu içeren makrohalkalı taç eter türevleri sentezlendi. Elde edilen 12-taç-4, 15-taç-5 ve 18-taç-6 bileşikleri kolon kromatografisi yöntemiyle saflaştırıldı. Sentezlenen benzokumarin ve benzokumarin türevi taç eterlerin yapıları UV,IR ve 1H-NMR spektrumlarıyla aydınlatıldı. Mart, 2004 Zehra ATAY
THE SYNTHESIS OF SOME NOVEL CROWN ETHER DERIVATIVES OF BENZOCOUMARIN COMPOUNDS AND CHARACTERIZATION OF THEIR STRUCTURE Coumarin (2H-1-benzopyran-2-one) derivatives are an important class of natural compounds having pharmaceutical activities. These compounds have many effects such as anticarcinogenecity, antifungal, anticoagulant, fluorescence and many investigations have been performed related to them. In this study, the synthesis of novel benzocoumarin compounds were performed. The structures of new coumarin-crown ethers were determined. 3-(3,4-Dimethoxyphenyl)coumarin and 5,6-benzo-3-(3,4-dimethoxhyphenyl)coumarin were synthesized by Perkin Reaction. 3-(3,4-Dihydroxyphenyl)coumarin and 5,6-benzo-3-(3,4-dihydroxhyphenyl)coumarin were obtained by demethylation reaction. 5,6-benzo-3-(3,4-dihydroxhyphenyl)coumarin was purifed by chrystallization from ethanol. The synthesis of novel 12-crown-4,15-crown-5, 18-crown-6 derivatives of this coumarin were performed. The purification of crown compounds were made by using silica gel column chromatography. The structures of new coumarin-crown ethers were determined based on the results of spectroscopic methods such as UV, IR and 1H-NMR. March, 2004 Zehra ATAY
THE SYNTHESIS OF SOME NOVEL CROWN ETHER DERIVATIVES OF BENZOCOUMARIN COMPOUNDS AND CHARACTERIZATION OF THEIR STRUCTURE Coumarin (2H-1-benzopyran-2-one) derivatives are an important class of natural compounds having pharmaceutical activities. These compounds have many effects such as anticarcinogenecity, antifungal, anticoagulant, fluorescence and many investigations have been performed related to them. In this study, the synthesis of novel benzocoumarin compounds were performed. The structures of new coumarin-crown ethers were determined. 3-(3,4-Dimethoxyphenyl)coumarin and 5,6-benzo-3-(3,4-dimethoxhyphenyl)coumarin were synthesized by Perkin Reaction. 3-(3,4-Dihydroxyphenyl)coumarin and 5,6-benzo-3-(3,4-dihydroxhyphenyl)coumarin were obtained by demethylation reaction. 5,6-benzo-3-(3,4-dihydroxhyphenyl)coumarin was purifed by chrystallization from ethanol. The synthesis of novel 12-crown-4,15-crown-5, 18-crown-6 derivatives of this coumarin were performed. The purification of crown compounds were made by using silica gel column chromatography. The structures of new coumarin-crown ethers were determined based on the results of spectroscopic methods such as UV, IR and 1H-NMR. March, 2004 Zehra ATAY