Synthesis of Different Substituted Isocoumarin Derivatives Using Zinc Triflate Catalyst

Abstract

Coumarins, which constitute a large class of natural compounds, are organic compounds that have attracted interest since the 19th century and have numerous practical applications. Coumarin compounds are heterocyclic compounds found in industry and in the structure of many commercial drugs. In this study, zinc-triflate-catalyzed tandem reactions of methyl 2-(phenylethyl) benzoate with but-3-en-2-one were applied for the synthesis of isocoumarins by a different method. The reaction was carried out under oxygen-free conditions using a convenient and environmentally benign reaction method in high yields and synthesized the targeted isoquamarine derivatives in a single step with the help of a novel catalyst. In addition, the effect of electron-withdrawing-electron-donating side groups on the formation and percentage yield of the reaction was investigated in this study. In summary, in this study, cascada reaction with palladium (II)-catalyzed highly regioselective but-3-en-2-one was developed.

Keywords

• Isocoumarin
• Antimicrobial
• Lactone
• Inhibitor
• Biological property
• Cascada

Çinko-Triflat Katalizörü Kullanılarak Farklı Sübstitüe Izokumarin Türevlerinin Sentezi

Abstract

Geniş bir doğal bileşik sınıfı oluşturan kumarinler, 19. yüzyıldan günümüze değin oldukça ilgi çeken ve çok sayıda pratik uygulamaya sahip olan organik bileşiklerdir. Kumarin bileşikleri, endüstride ve birçok ticari ilacın yapısında bulunan heterosiklik bileşikler olup, bu çalışmada izokumarinlerin sentezleri için farklı bir yöntem izlenerek metil 2-(feniletil) benzoat (1a-g) ve but-3-en-2-one (2)’nin çinko-triflat-katalizli tandem reaksiyonları gerçekleştirilmiştir. Söz konusu yöntemde, yüksek verimli ve çevre dostu bir reaksiyon oksijensiz ortamda gerçekleştirilmiş ve yeni bir katalizör kullanılarak hedeflenen izokumarin türevleri tek basamakta sentezlenmiştir. Diğer taraftan, elektron çekici ve elektron verici yan grupların reaksiyon oluşumuna ve verimine olan etkileri de araştırılmıştır. Özet olarak bu çalışmada, paladyum(II)-katalizli yüksek oranda regioselektif but-3-en-2-one ile cascada reaksiyonu ile geliştirilmiştir.

Keywords

• İzokumarin
• Antimikrobiyal
• Lakton
• İnhibitör
• Biyolojik özellik
• Cascada

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