藉由銅催化級聯反應將 2-碘聯苯醯胺衍生物與 2-炔基芐基氰化物合成出二苯並[c,f][1,8]萘啶-5(6H)-酮衍生物與亞氨基異吲哚衍生物

Synthesis of dibenzo[c,f][1,8]naphthyridine-5(6H)-one and iminoisoindole derivatives via copper-catalyzed tandem reaction of substituted 2-iodobenzamides and 2-alkynylbenzylcyanides

黎准滺(Li Chun-You)

指導教授 ： 姚清發

國立臺灣師範大學/理學院/化學系/碩士(2020年)

https://doi.org/10.6345/NTNU202001258

摘要

本論文分為兩個章節。第一章為緒論，包括對 1,8-萘啶的介紹與其衍生物的合成和性質的文獻回顧。本章節還介紹了有關異吲哚啉1-酮的衍生物、銅催化反應、區域選擇性轉換反應與薗頭反應的文獻回顧。在末尾的部份，我們還敘述了研究目標與動機。
第二章分為兩個部份。第一部份為利用 2-碘苯甲醯胺與 2-溴苯基乙炔進行薗頭偶聯反應，進一步得到相應的亞氨基異吲哚啉-1-酮衍生物，並在後續鈀催化條件下進行赫克反應，分子內合環後得到相應的苯並稠合的異吲哚啉-1-酮衍生物。另一部分為在碳酸銫的鹼性條件下以二甲基亞碸為溶劑，將 2-氨基苯甲醯胺衍生物和 2-炔基芐基氰化物進行銅催化級聯反應得到 1,8-萘啶衍生物，並在碳酸鉀的條件下製備出亞氨基異吲哚衍生物。

關鍵字

none

並列摘要

This thesis is divided in two chapters. The first chapter dealt with preface of the thesis which includes the introduction to 1,8-naphtharidine derivatives and literature survey on the synthesis and properties of 1,8-
naphtharidine derivatives. In addition, this chapter introduce short literature descriptions about isoindolinone derivatives, copper catalyzed reactions, regioselective-switching reactions and Sonogashira coupling reactions. Further, we then disclosed the aim and research goals at the end of the first chapter.
The second chapter consists two parts. The first part describes about the synthesis of 1,8-naphtharidine derivatives through copper catalyzed tandem cyclization of 2-idobenzamide derivatives and 2-alkynylbenzylcyanides in DMSO using cesium carbonate as base and further the same reaction furnished iminoisoindole derivatives using
potassium carbonate as base.
The next part is Sonogashira coupling reaction of 2-iodobenzamide derivatives and 2-bromophenylacetylenes to obtain corresponding isoindolinone derivatives. The resulted isoindole derivatives further converted into corresponding benzofusedisoindolinone derivatives through
palladium catalyzed Heck coupling.

並列關鍵字

none

參考文獻

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