Convenient construction of spiro[indoline-3,5’-pyrrolo[3,4-c]carbazole]and spiro[indene-2,5’-pyrrolo[3,4-c]carbazole]via acid-catalyzed Diels-Alder reaction  

作　　者：Chen Yan Jing Sun Chao-Guo Yan 

机构地区：[1]College of Chemistry&Chemical Engineering,Yangzhou University,Yangzhou 225002,China

出　　处：《Chinese Chemical Letters》2021年第3期1253-1256,共4页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China(No.21572196);the Priority Academic Program Development of Jiangsu Higher Education Institutions,China。

摘　　要：p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with 3-phenacylideneoxindoles in toluene at 80℃for two hours afforded cis/trans isomers of 3 a’,4’,6’,10 c’-tetrahydrospiro[indoline-3,5’-pyrrolo[3,4-c]carbazoles]in nearly comparable yields,which could be easily converted to the corresponding 4’,6’-dihydrospiro[indoline-3,5’-pyrrolo[3,4-c]carbazole]in high yields and with high diastereoselectivity by further DDQ oxidation.Additionally,the similar reaction of 3-(indol-3-yl)maleimides with 2-arylidene-1,3-indanediones in toluene 80℃and sequential DDQ oxidation afforded functionalized dihydrospiro[indene-2,5’-pyrrolo[3,4-c]carbazoles]as major products.

关 键 词：CARBAZOLE Spiroixindole MALEIMIDES 1 3-Indanedione Diels-Alder reaction 

分 类 号：O626[理学—有机化学]