Issue 10, 2010

Regioselective synthesis of 3-acylindolizines and benzo- analogues via1,3-dipolar cycloadditions of N-ylides with maleic anhydride

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Jan 2010
Accepted
08 Mar 2010
First published
24 Mar 2010

Org. Biomol. Chem., 2010,8, 2449-2456

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

Y. Liu, Y. Zhang, Y. Shen, H. Hu and J. Xu, Org. Biomol. Chem., 2010, 8, 2449 DOI: 10.1039/C000277A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements