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] Institute of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China; [2] School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, Jiangsu, China; [3] Institute of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China; [4] Key Laboratory of Analytical Chemistry for Life Science, Ministry of Education, Nanjing 210093, China

年份：2010

卷号：8

期号：10

起止页码：2449

外文期刊名：Organic and Biomolecular Chemistry

收录：EI(收录号：20102012938461)、Scopus(收录号：2-s2.0-77952394193)

语种：英文

外文关键词：Carboxylation - Cycloaddition - Regioselectivity - Chromates

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. ? 2010 The Royal Society of Chemistry.