KARBONİL GRUPLARININ REGİOSELEKTİF OLARAK İNDİRGENMESİ VE SEKONDER ALKOLLERİN ELDESİ
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Tarih
2020-12-31
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info:eu-repo/semantics/openAccess
Özet
Karbonil gruplarının indirgenmesi antifungal, antidepresan, antitüberküler aktiviteye sahip siklik amid türevleri gibi biyolojik aktiviteye sahip bileşiklerin sentezlenmesi ve primer, sekonder ve tersiyer alkoller elde etmek için sıklıkla kullanılmaktadır. Bu çalışmada, keton ve amid karbonil grublarını birlikte barındıran bileşiklerimiz diğer yöntemlere göre daha seçici olması, güvenli yapısı, yüksek verimli ve temiz ürünler sunması nedeniyle sodyum borhidrür (NaBH4) ile indirgenmiştir. Bu şekilde ilaçların, tarım kimyasallarının, gıda kimyasallarının ve diğer saf kimyasalların sentezi için oldukça önemli bileşiklerden olan sekonder alkoller regioselektif olarak elde edilmiştir. Bunun için başlangıç bileşiği olan 2-(5-amino-1,3,4-tiyadiazol-2-iltiyo)-1-(3,4-diklorofenil)ethanon (3) elde edilmiştir. Daha sonra bu (3) nolu bileşiğin uygun sübstitüe açil halojenür türevleriyle (4a-j) olan reaksiyonundan sonuç bileşiğinin ilk grubu olan 10 adet yeni 2-amino-1,3,4-tiyadiazol’ün açil türevleri (5a-j) sentezlenmiştir. Çalışmamızın son adımında ise yapısında keton ve amid karbonil grublarını birlikte barındıran 2-amino-1,3,4-tiyadiazol’ün açil türevlerinin (5a-j) NaBH4 ile regioselektif indirgenmesinden sekonder alkol türevleri olan bileşiklere (6a-j) varılmıştır. Çalışmamızda elde edilen toplam 20 maddenin moleküler yapıları 1H-NMR, 13C-NMR, FT-IR, MS gibi spektroskopik analizörler kullanılarak aydınlatılmıştır. ?
Reduction of carbonyl groups is commonly used to synthesize compounds with biological activity such as antifungal, antidepressant, cyclic amide derivatives with antitubercular activity, and to obtain primary, secondary and tertiary alcohols. In this study, our compounds containing ketone and amide carbonyl groups together were reduced with sodium borohydride (NaBH4) because they are more selective than other methods, safe structure, high efficiency and clean products. In this way, secondary alcohols, which are very important compounds for the synthesis of drugs, agricultural chemicals, food chemicals and other pure chemicals, were obtained regioselectively. For this, the starting compound 2-(5-amino-1,3,4-thiadiazol-2-ylthio)-1-(3,4-dichlorophenyl) ethanone (3) was obtained. Then the reaction of this compound (3) with the appropriate substituted acyl halide derivatives (4a-j) were synthesized from the first group of the resulting compound, 10 acyl derivatives (5a-j) of 14 new 2-amino-1,3,4-thiadiazole. In the last step of our study, the compounds (6a-j) which are the secondary alcohol derivatives from the regioselective reduction of the acyl derivatives (5a-j) of 2-amino-1,3,4-thiadiazole together with the ketone and the amide carbonyl groups together with the NaBH4 were reached. The molecular structures of a total of 20 substances obtained in our study were elucidated using spectroscopic analyzers such as 1H-NMR, 13C-NMR, FT-IR, MS."
Reduction of carbonyl groups is commonly used to synthesize compounds with biological activity such as antifungal, antidepressant, cyclic amide derivatives with antitubercular activity, and to obtain primary, secondary and tertiary alcohols. In this study, our compounds containing ketone and amide carbonyl groups together were reduced with sodium borohydride (NaBH4) because they are more selective than other methods, safe structure, high efficiency and clean products. In this way, secondary alcohols, which are very important compounds for the synthesis of drugs, agricultural chemicals, food chemicals and other pure chemicals, were obtained regioselectively. For this, the starting compound 2-(5-amino-1,3,4-thiadiazol-2-ylthio)-1-(3,4-dichlorophenyl) ethanone (3) was obtained. Then the reaction of this compound (3) with the appropriate substituted acyl halide derivatives (4a-j) were synthesized from the first group of the resulting compound, 10 acyl derivatives (5a-j) of 14 new 2-amino-1,3,4-thiadiazole. In the last step of our study, the compounds (6a-j) which are the secondary alcohol derivatives from the regioselective reduction of the acyl derivatives (5a-j) of 2-amino-1,3,4-thiadiazole together with the ketone and the amide carbonyl groups together with the NaBH4 were reached. The molecular structures of a total of 20 substances obtained in our study were elucidated using spectroscopic analyzers such as 1H-NMR, 13C-NMR, FT-IR, MS."
Açıklama
Anahtar Kelimeler
Secondary Alcohol, Regioselective Reduction, 1, 3, 4-Thiadiazole, Sekonder alkol, Regioselektif indirgenme, 1, 3, 4-Tiyadiazol
