文献类型：期刊文献

英文题名：Regioselective synthesis of 3-acylindolizines and benzo- analogues via 1,3-dipolar cycloadditions of N-ylides with maleic anhydride

作者：Liu, Yun[1,2];Zhang, Yan[1,4];Shen, Yong-Miao[3];Hu, Hong-Wen[1];Xu, Jian-Hua[1]

机构：[1]Nanjing Univ, Inst Chem & Chem Engn, Nanjing 210093, Peoples R China;[2]Xuzhou Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China;[3]Shaoxing Univ, Inst Chem & Chem Engn, Shaoxing 312000, Peoples R China;[4]Minist Educ, Key Lab Analyt Chem Life Sci, Nanjing 210093, Peoples R China

年份：2010

卷号：8

期号：10

起止页码：2449

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：SCI-EXPANDED(收录号：WOS:000277399300023)、、WOS、CCR-EXPANDED(收录号：WOS:000277399300023)

基金：This work was supported by the NSFC (20272024, 20742002), 41th China Planned Projects for Postdoctoral Research Funds (20070411027), Jiangsu Planned Projects for Postdoctoral Research Funds (0701009B), and Natural Science Foundation of Jiangsu Province (BK 2007132).

语种：英文

外文关键词：Carboxylation - Chromates - Cycloaddition - Maleic anhydride - Reagents

外文摘要：3-Acylindolizines (5a-5f) and their benzo-analogues 1-acylpyrrolo[1,2-a]quinolines (6a-6f) and 1-acylpyrrolo[2,1-a]isoquinolines (7a-7i) are regioselectively synthesized by a convenient one pot reaction of the corresponding pyridinium (quinolinium, isoquinolinium) ylide with maleic anhydride (MA) in the presence of the mild oxidant tetrakispyridinecobalt(II) dichromate (TPCD). These reactions proceed via a tandem reaction sequence of 1,3-dipolar cycloaddition of azomethine ylide with MA, anhydride hydrolysis and oxidative bisdecarboxylation of the primary cycloadducts followed by dehydrogenative aromatization of the dihydroindolizines. TPCD serves as both decarboxylation and dehydrogenation reagent in the reactions. These results show that TPCD is a promising new reagent for bisdecarboxylation of aliphatic carboxylates.