Copper Catalyzed Cascade Approaches for the syntheses of diverse Heterocyclic compounds Using 2-halo benzamide and 2-halobenzylcyanide derivatives

Abstract

本論文的內容分為三個部分(A，B和C部分)，A部分包括介紹以及概論銅級聯催化反應，包含詳細討論級聯反應以及不同級聯反應。此次的的討論除了級聯反應部分，還包含不同的一個、兩個、三個甚至四個的新鍵。此外，還敘述了有趣的雜環銅催化級聯反應。B部分包含兩個部分。第一部分從文獻中利用2-鹵代苯甲酰胺衍生物合成多種雜環化合物。第二部分，從2-碘苯甲酰胺衍生物合成螺異吲哚啉酮 - 吲哚啉和1,2-二取代吲哚。最後，C部分有三個部分。第一部分文獻中利用2-鹵代芐基氰化物衍生物合成各種雜環化合物。第二部分中，敘述了利用銅催化級聯反應合成二苯並[1,8]萘啶衍生物。第三部分，敘述了利用銅催化級聯反應合成合成2-芳基-3-氰基苯並呋喃和二苯並[b，f]氧雜-10-甲腈衍生物。

本文所敘述的銅催化級聯反應，利用2-鹵代苯甲酰胺和2-鹵代芐基氰化物合成多種雜環化合物，包含了1,2-二取代吲哚，2-鹵代苯甲酰胺和苯並呋喃取代的異吲哚啉酮和螺異吲哚啉酮衍生物，oxepin衍生物和和2-鹵代芐基氰化物取代的1,8-二氮雜萘衍生物 本篇合成雜環的反應為烏爾曼偶聯，Sonagashira偶聯，氫化胺化，氫化酰胺化，oxa-Michael加成，Knoevenagel縮合和氧化。The contents of this dissertation are divided into three Sections. (Section A, B& C). Section A includes introduction and overview on Copper catalyzed cascade reactions describing the detailed definitions of Cascade reactions and differentiation of cascade reactions. This section intern includes variety of copper catalyzed cascade reactions which involves the formation of two, three and four new bonds. A variety of interesting miscellaneous copper catalyzed cascade reactions was also described. Section B contains two parts. In part I, the syntheses of diverse heterocyclic compounds using 2-halobenzamide derivatives were compiled from the literature. In part II, the Syntheses of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives were described. Finally, Section C contains three parts. In part I, the syntheses of diverse heterocyclic compounds using 2-halobenzylcyanide derivatives were compiled from the literature. In part II, a copper catalyzed cascade approach for the synthesis of Dibenzo1,8-naphthyridine derivatives was described. In part III, copper catalyzed cascade approach for the synthesis of 2-Aryl-3-cyanobenzofurans and Dibenzo[b,f]oxepine-10-carbonitrile derivatives was described.

The copper catalyzed cascade synthetic protocol described in this dissertation was applied to 2-halobenzamides and 2-halobenzylcyanides, respectively, to synthesize diverse heterocyclic compounds which includes 1,2- disubstituted Indoles, Isoindolinone derivatives and spiro isoindolinone-indoline derivatives with respect to 2-halobenzamides and benzofurans, oxepin derivatives and 1,8-naphthyridine derivatives with respect to 2-halobenzylcyanides. The reactions involved in this protocol for the syntheses of these heterocycles were Ullmann coupling, Sonagashira coupling, Hydro amination, Hydro amidation, Oxa-Michael addition, Knoevenagel condensation and oxidation.