2,6-bis(pirolilmetil)piridinlerin sentezi
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Dosyalar
Tarih
2009
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Kırıkkale Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Piroller, doğada çok yaygın olarak bulunan ve hem malzeme bilimleri hem de doğal ürünlerin sentezinde kullanılan ilginç alt birimlerdir. Pirollerin antioksidan oldukları, P38 kinaz inhibitörleri ve pirolil-4-hidroksilaz inhibitörleri oldukları gösterilmiştir. Ayrıca, pirollerin metal bağlama özellikleri üzerinde de ciddi bir çalışma vardır. Böylece yeni katalitik sistemler elde edilmektedir. Pirol türevlerinin böylesine değerli ve çok çeşitli özellikleri, çok fazla metodun yayınlanmasına rağmen, yeni metotların gelişmesine yol açmaktadır.Bu çalışmada, 2,6-dimetilpiridinden başlayarak 2,6-bis(pirolilmetil)piridinler sentezlenmiştir. İlk basamakta, 2,6-dimetilpiridin N-klorosüksinimit ile reaksiyona sokularak 2,6-bis(klorometil)piridin elde edilmiştir. İkinci basamakta, bu ürün potasyum ftalimit ile muamele edilerek 2,6-bis(aminometil)piridine çevrilmiştir. Üçüncü basamakta, amin bileşiği çeşitli kloroenonlarla tepkimeye sokularak 1,2-disübstitüe (pirolilmetil)piridin ve 1,2,4-trisübstitüe (pirolilmetil)piridin türevleri elde edilmiştir. Bu bileşikler, hem pirol hem de piridin birimlerini içermelerinden dolayı çok çeşitli amaçlarla kullanılabilecek önemli ara ürünlerdir. Bu çalışma ile 2,6-bis(pirolilmetil)piridinlerin sentezi için kolay, uygulanabilir ve kısa bir metot geliştirilmiştir.
Pyrroles are widely present in nature and are interesting subnits for both material sciences and natural product synthesis. They have been shown to be antioxidants. P38 kinase inhibitors, and prolyl-4-hydroxylase inhibitors. There has also been significant interest in the metal binding properties of them. Thus, new catalytic systems have been obtained. The valuable and diverse properties of pyrrole derivates lead to the development of new methods although numerous pathways have been reported.In this work, diverse 2,6-bis(pyrrolilmethyl)pyridines were synthesized starting from 2,6-dimethylpyridine. In the first step, 2,6-dimethylpyridine was reacted with N-chlorosuccinimide to get 2,6-bis(chloromethyl)pyridine. In the second step, this product was converted to 2,6-bis(aminomethyl)pyridine via potassium phthalimide. In the third step, 1,2-disubstituted (pyrrolylmethyl)pyridine and 1,2,4-trisubstituted (pyrrolylmethyl)pyridine derivates were obtained by the reaction of amine compound with diffrrent chloroenones. These compounds are important intermediates which can be used for diffrent purposes since they contain both pyrrole and pyridine units. By this work, an easy, applicable and a short method was developed for the synthesis of 2,6-bis(pyrrolylmethyl)pyiridines.
Pyrroles are widely present in nature and are interesting subnits for both material sciences and natural product synthesis. They have been shown to be antioxidants. P38 kinase inhibitors, and prolyl-4-hydroxylase inhibitors. There has also been significant interest in the metal binding properties of them. Thus, new catalytic systems have been obtained. The valuable and diverse properties of pyrrole derivates lead to the development of new methods although numerous pathways have been reported.In this work, diverse 2,6-bis(pyrrolilmethyl)pyridines were synthesized starting from 2,6-dimethylpyridine. In the first step, 2,6-dimethylpyridine was reacted with N-chlorosuccinimide to get 2,6-bis(chloromethyl)pyridine. In the second step, this product was converted to 2,6-bis(aminomethyl)pyridine via potassium phthalimide. In the third step, 1,2-disubstituted (pyrrolylmethyl)pyridine and 1,2,4-trisubstituted (pyrrolylmethyl)pyridine derivates were obtained by the reaction of amine compound with diffrrent chloroenones. These compounds are important intermediates which can be used for diffrent purposes since they contain both pyrrole and pyridine units. By this work, an easy, applicable and a short method was developed for the synthesis of 2,6-bis(pyrrolylmethyl)pyiridines.
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
