Bis (açilazidler):heterosiklik bileşiklerin sentezinde yeni bir kilometre taşı: furofuran, furopirol, pirolopiridin, piridopiridazin, piridoprimidinon, piroloindol, pirimidoindolon gibi bileşiklerin sentezi için yeni yöntemlerin geliştirilmesi

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2013

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Balcı, Metin
Koza, Gani
Doğan, Dilem Şengül
Keskin, Selbi
Dinçoflaz, Yasemin
Özer, Sinem Merve
Ergun, Merve
Kaptı, Tolga

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Basit heterosiklik bileşikler arasında iki heterosiklik bileşik vardır ki bunlar çok farklı özellikler sergilerler. Bunlardan birisi pirol, diğeri ise piridindir. Pirol; elektronca zengin, aromatik özelliğe sahip, kolay polimerleşen, asitlere karşı duyarlı, bazik özellik göstermeyen ve elektrofillerle kolayca tepkime veren bir bileşiktir. Piridin ise elektronca fakir, bazik özelliğe sahip, aromatik, elektrofilik tepkimelere karşı dayanıklı, fakat nükleofillerle tepkime veren bir bileşiktir. Bu moleküllerin farklı davranışları, her iki bileşiğin rezonans yapılarından kolayca anlaşılmaktadır. Bu iki heteroaromatik bileşiğin kenetlenmesi veya bu bileşiklere benzen, furan gibi halkaların bağlanması ile ilginç moleküller oluşmaktadır. Bu proje kapsamında, yeni heterosiklik bileşiklerin sentezi için benzen ve heterosiklik aromatik diasitlerden çıkıldı. Piridazinon türevlerinin sentezi için önce metilen grubu ilgili ketona yükseltgendi. Daha sonra ketoesterlerin hidrazin ile tepkimesi sonucu oluşan hidrazonların intramoleküler siklizasyonu ile ilgili halkalara kenetlenmiş pridazinon iskeleti oluşturuldu. Diğer ester grubunun amine indirgenmesi ile aminopiridazinon türevleri elde edildi. Projenin başka bir bölümünde asit gruplarından birisi amide diğer asit grubu açil azide çevrildi. Curtius düzenlenmesi sonucu oluşan izosiyanata amit azot atomunun katılması sağlandı ve ilk kez literatürde önemli biyolojik aktivite gösterme potansiyeline sahip furo- ve tiyeno-1,3-diazepin-2,4-dion türevlerinin sentezi gerçekleştiridi. Piridin halkasıyla yapılan çalışmalarda asit gruplarından birisi ester olarak korunurken diğeri açil azide çevrildi. Piridin halkasıyla yapılan çalışmalarda ise doğrudan halkaya bağlı olan asit grubu açil azid üzerinden önce ilgili izosiyanata çevrildi ve daha sonra diğer metilen grubu ile enol formu üzerinden siklizasyon gerçekleştirildi. Böylece pirolopiridin türevleri sentezlendi.

Subject Keywords

Fitalazinon, Aminoftalazinon, Furopiridazinon Tiyeno-piridazinon, Furo-diazepindion, Tiyeno-diazepindion, Pirolopiridinon

URI

https://app.trdizin.gov.tr/publication/project/detail/TVRJNU1EVTE
https://hdl.handle.net/11511/49469

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Department of Chemistry, Project and Design

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Citation Formats

M. Balcı et al., “Bis (açilazidler):heterosiklik bileşiklerin sentezinde yeni bir kilometre taşı: furofuran, furopirol, pirolopiridin, piridopiridazin, piridoprimidinon, piroloindol, pirimidoindolon gibi bileşiklerin sentezi için yeni yöntemlerin geliştirilmesi,” 2013. Accessed: 00, 2020. [Online]. Available: https://app.trdizin.gov.tr/publication/project/detail/TVRJNU1EVTE.