銅催化合成多種類芳基醯胺呋喃及羥基異吲哚啉酮衍生物

Copper Catalyst for the Synthesis of Various Aryl Amido Furans and Hydroxyisoindolinone Derivatives

謝孟諠(Hsieh Meng-Hsuan)

指導教授 ： 姚清發

國立臺灣師範大學/理學院/化學系/碩士(2016年)

https://doi.org/10.6345/NTNU202204736

摘要

本篇論文主要分為兩章節，兩章節各自包含前言、研究目標、實驗結果與討論，以及結論。第壹章節以2-碘-N-苯基苯甲醯胺與炔基化合物當作起始物，進行銅試劑串聯薗頭耦合反應及分子內環化反應合成具有三取代基的呋喃化合物，此反應利用碘化亞銅催化及碳酸銫鹼試劑在溫和的條件下成功合成，這提供一種較快速且高產率合成多取代呋喃化合物的方法。
第貳章節承接第壹章節的部分內容，主要探討3-羥基異吲哚啉酮的合成方法，同樣以2-碘-N-苯基苯甲醯胺與炔基化合物當作起始物，在一鍋化的條件下，利用二甲基亞碸當作溶劑及碘化亞銅為催化劑，合成多取代的呋喃化合物後，接著在氧氣環境下合成3-羥基異吲哚啉酮的化合物。我們在單一反應中探索多功能銅催化試劑的用途，此反應能在相對較短的時間內進行碳-碳鍵的耦合與碳-氫鍵的氧化反應。

關鍵字

呋喃 ； 異吲哚啉酮 ； 薗頭耦合反應

並列摘要

The contents of thesis is mainly divided into two chapters and further, each chapter individually included preamble, research goal, results description and conclusion. In the first chapter, deals with a copper catalyzed tandem Sonogashira coupling reaction and cycloisomerization for the synthesis of trisubstituted furans derivative from 2-iodo-N- phenylbenzamide derivative and 3-propargyl-1,3-diketone in the presence of copper iodide and cesium carbonate mild conditions, moderate to good yields, rapid reactions are important features of this methodology.
The second project deals with the synthesis of 3-hydroxy- isoindolinone possessing furan substituent through a one pot reaction of 2-iodo-N- phenylbenzamide and 3-propargyl 1,3-diketone derivatives in the presence of copper iodide and cesium carbonate in DMSO under oxygen atmosphere. In the present methodology, we explore multiple roles of copper catalyst in single reaction. C-C coupling reaction, alkyne activation, and C-H oxidation in one pot was happened in very short time.

並列關鍵字

Furan ； isoindolinone ； Sonogashira coupling

參考文獻

第壹章、銅催化串聯耦合及環化異構化反應合成多種類的芳基醯胺呋喃化合物

1. Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.

2. Chinchilla, R. Na´jera, C. Chem. Rev. 2007, 107, 874.

3. (a) Diek, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259. (b) Cassar, L. J. Organomet. Chem. 1975, 93, 253. (c) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.

4. Saito, A.; Enomoto, Y.; Hanzawa, Y. Tetrahedron Lett. 2011, 52, 4299.