- 學位論文
一、2-碘苯甲醯胺衍生物和炔丙基二羰基化合物以銅金屬催化進行氧化級聯雙環化反應合成3-羥基-3-呋喃基異吲哚酮衍生物 二、以一鍋化方法進行克腦文蓋爾縮合反應/亞胺化/π-Aza 電環化合成三取代吡啶 三、以銅金屬進行串連環化異吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和 5,13-二氫11H-喹唑啉 [2,3-b]喹唑啉-11-酮衍生物
1.Copper Catalyzed Oxidative Cascade Double Cyclization of 2--Iodobenzamide Derivatives and Propargyl dicarbonyl Compounds for Accessing 3-Hydroxy-3-furylisoindoli¬none derivatives 2.One-Pot Three-Component Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Trisubstituted Pyridines 3.Synthesis of Isoindolo [1,2-b]quinazolin-12(10H)-one and 5,13-dihydro-11H quinazolino[2,3-b]quinazolin-11-one Derivatives via Copper Catalyzed Tandem Cyclization
摘要
一:利用2-碘苯甲醯胺衍生物和炔丙基二羰基化合物作為起始物並利用銅催化促成氧化級聯分子間雙環化來進行3-羥基-3-呋喃基異吲哚啉酮衍生物的一鍋化合成。本次的策略包含環化反應、偶聯反應、雙C(sp3)-H官能化。本次合成3-羥基-3-呋喃基異吲哚啉酮衍生物的策略是利用不同取代基的2-碘苯甲醯胺衍和各種不同的炔丙基二羰基及炔丙基磺醯基芳基酮。 二:我們開發出一種以溴丙烯醛、苯甲醯乙腈和乙酸銨為起始物並利用銅金屬進行催化反應歷經三個不同反應後生成三取代吡啶。3-溴丙烯醛與苯甲醯乙腈會先進行克腦文蓋爾縮合反應形成2,4-二烯酮隨後和氨進行反應，並生成相應的氮雜三烯。最後經過6π-氮雜電環化/芳構化反應並生成三取代的吡啶。 三:我們開發出一種反應過程簡單、產率高的一鍋化方法，透過銅催化將N-(2-溴芐基)-2-碘苯甲醯胺的進行串聯反應而合成出吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和氰化銅
並列摘要
1.One-pot strategy is reported for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives via copper catalyzed oxidative cascade inter-molecular double cyclisation of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The present strategy involves several reactions including cyclization/coupling/double C(sp3)-H functionalization in cascade manner. Wide range of 2-iodobenzamide substrates having different substituents as well as various propargyldicarbonyl and propargylsulfonyl aryl ketones are used to access variety of 3-hydroxy-3-furylisoindolinone derivatives in the present methodology. 2. A facile copper-catalyzed three-component reaction for the synthesis of trisubstituted pyridines from 3-bromopropenals, benzoylacetonitriles, and ammonium acetate (NH4OAc) is developed. The Knoevenagel-type condensation of 3-bromopropenal with benzoylacetonitrile gives 2,4-dienone with strategically placed functional groups, which reacts with in situ generated ammonia to give the corresponding azatriene. A subsequent reaction sequence of 6π-azaelectrocyclization/aromatization produces a trisubstituted pyridine under the reaction conditions. 3.Herein, we developed a simple and one pot method for the synthesis of isoindolo [1,2-b]quinazolin-12(10H)-one derivatives via copper catalyzed tandem reaction of N-(2-bromobenzyl)-2-iodobenzamide as substrate and copper cyanide. The procedure is easy, simple and the yields are good to excellent.