1227796-78-2Relevant articles and documents
CuBr-Catalyzed Aerobic Decarboxylative Cycloaddition for the Synthesis of Indolizines under Solvent-Free Conditions
Wang, Wenhui,Han, Junwen,Sun, Jinwei,Liu, Yun
, p. 2835 - 2842 (2017)
An efficient synthesis of diversified indolizine derivatives was developed via CuBr-catalyzed reaction of pyridines, methyl ketones and alkenoic acids under solvent-free conditions in oxygen atmosphere. This synthesis involves cascade processes of copper-catalyzed bromination of the methyl ketone, 1,3-dipolar cycloaddition of the pyridinium ylide with the alkenoic acid, followed by oxidative decarboxylation and dehydrogenative aromatization of the primary cycloadduct. By this protocol, a wide range of indoliznes with different substitution patterns were selectively prepared in one pot from simple substrates in good to excellent yields.
Regioselective synthesis of 3-acylindolizines and benzo- analogues via 1,3-dipolar cycloadditions of N-ylides with maleic anhydride
Liu, Yun,Zhang, Yan,Shen, Yong-Miao,Hu, Hong-Wen,Xu, Jian-Hua
experimental part, p. 2449 - 2456 (2010/07/09)
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.