Yun Liu, Yan Zhang, Yong-Miao Shen
May 6, 2010
Citations
0
Influential Citations
40
Citations
Journal
Organic & biomolecular chemistry
Abstract
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.