Synthesis of New Isoindole-1,3-dione Derivatives Containing Halohydrin Unit

Öz

In this study, the reaction of 2-(benzyl/ethyl/phenyl/methyl)-3a,4,7,7a-tetrahydro-1Hisoindole-1,3-(2H)-dione compounds with m-CPBA (m-chloroperbenzoic acid) has been examined. Syn-epoxides were obtained as the main product from the epoxidation reactions. Then, ring opening reactions of syn-epoxides with HBr and HCl were carried out. Eight different isoindole derivatives containing halohydrin units were synthesized from epoxide ring opening reactions in stereocontrol. The structures of the synthesized compounds were elucidated using spectroscopic methods. Thus, starting or precursor compounds were obtained for the synthesis of polyfunctional derivatives containing isoindole-1,3-dione main skeletal structure using easy and applicable methods.

Anahtar Kelimeler

• Epoxides
• ring opening reaction
• isoindol-1
• 3-dione
• halohydrin

Halohidrin Birimi İçeren Yeni İsoindol-1,3-dion Türevlerinin Sentezi

Öz

Bu çalışmada, 2–(benzil/etil/fenil/metil)-3a,4,7,7a-tetrahidro-1H-isoindol-1,3-(2H)-dion bileşiklerinin m-KPBA (m-kloroperbenzoik asit) ile reaksiyonları incelendi. Epoksidasyon reaksiyonlarından ana ürün olarak syn-epoksitler elde edildi. Daha sonra syn-epoksitlerin HBr ve HCl ile halka açılma reaksiyonları gerçekleştirildi. Epoksit halka açılma reaksiyonlarından halohidrin birimi içeren sekiz farklı isoindol türevi stereokontrollü olarak sentezlendi. Sentezlenen bileşiklerin yapıları spektroskopik yöntemler kullanılarak aydınlatıldı. Böylece kolay ve uygulanabilir yöntemler kullanılarak isoindol-1,3-dion ana iskelet yapısı içeren polifonksiyonel türevlerin sentezi için başlangıç veya öncü bileşikler elde edildi.

Anahtar Kelimeler

• Epoksitler
• halka açılma reaksiyonu
• isoindol-1
• 3-dion
• halohidrin

Teşekkür

Bu çalışmanın gerçekleşmesine katkı sağlayan Atatürk Üniversitesi Fen Fakültesi Kimya Bölümü’ne ve Kırşehir Ahi Evran Üniversitesi Kaman MYO’na teşekkür ederim.

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