Issue 21, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 1,2-annulated and 1,2-unsubstituted pyrrolo[2,1,5-de]quinolizin-5-ones (cycl[3.3.2]azin-5-ones) via [3+2] cycloadditions of 1-oxoquinolizinium ylides with cyclic alkenes†

Yun Liu,ab   Hua-You Hu,c   Yan Zhang,ad   Hong-Wen Hua  and  Jian-Hua Xu*a  

* Corresponding authors

a Institute of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China
E-mail: xujh@nju.edu.cn
Fax: +86 25 83317761
Tel: +86 25 83592709

b Institute of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, Jiangsu, P. R. China

c Institute of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, PR China

d Key Laboratory of Analytical Chemistry for Life Science, Ministry of Education, Nanjing 210093, PR China

Abstract

1,2-Annulated pyrrolo[2,1,5-de]quinolizin-5-ones (cycl[3.3.2]azin-5-ones) 6a–6k, 8a–8b and 9 have been synthesized by one pot tandem reactions of 2-acetyl-N-phenacylpyridinium bromides (1a–1d) with electron-deficient cyclic alkenes (N-alkyl(aryl)maleimides, benzoquinones and naphthoquinone) in the presence of sodium carbonate as a base and tetrakispyridinecobalt(II) dichromate (TPCD) as an oxidant. These products are formed by 1.3-dipolar cycloaddition of the 1-oxoquinolizinium ylides generated in situ from 1a–1d with the alkene followed by dehydrogenation of the primary cycloadduct under the action of TPCD. Similar reactions of the ylides generated in situ from 1a–1f with maleic anhydride gave the 1,2-unsubstituted pyrrolo[2,1,5-de]quinolizin-5-ones 7a–7f via oxidative bisdecarboxylation and dehydrogenation of the primary cycloadducts under the action of TPCD.

Graphical abstract: Synthesis of 1,2-annulated and 1,2-unsubstituted pyrrolo[2,1,5-de]quinolizin-5-ones (cycl[3.3.2]azin-5-ones) via [3+2] cycloadditions of 1-oxoquinolizinium ylides with cyclic alkenes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0OB00299B
Article type
Paper
Submitted
22 Jun 2010
Accepted
14 Jul 2010
First published
26 Aug 2010

Org. Biomol. Chem., 2010,8, 4921-4926

Permissions

Request permissions

Synthesis of 1,2-annulated and 1,2-unsubstituted pyrrolo[2,1,5-de]quinolizin-5-ones (cycl[3.3.2]azin-5-ones) via [3+2] cycloadditions of 1-oxoquinolizinium ylides with cyclic alkenes

Y. Liu, H. Hu, Y. Zhang, H. Hu and J. Xu, Org. Biomol. Chem., 2010, 8, 4921 DOI: 10.1039/C0OB00299B

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