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Synthesis 2010(23): 4007-4014  
DOI: 10.1055/s-0030-1258266
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes

Huayou Hu*a, Kunbo Shia, Rongrong Houb, Zaichao Zhanga, Yulan Zhua, Jianfeng Zhoua
a Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P. R. of China
Fax: +86(517)83525100-1; e-Mail: huayouhu@hytc.edu.cn;
b Department of Chinese Language and Literature, Huaiyin Normal University, Huaian 223300, P. R. of China
Further Information

Publication History

Received 3 August 2010
Publication Date:
22 September 2010 (online)

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Abstract

3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high.

Key words

N-ylides - indolizine polycycles - 1,3-dipolar cycloadditions - one-pot reaction - electron-deficient alkenes

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Detailed X-ray crystallographic data for compound 4a (CCDC 760516) are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033, E-mail: deposit@ccdc.cam.ac.uk].