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Synthesis 2011(21): 3447-3452  
DOI: 10.1055/s-0030-1260215
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Synthesis of 2-Aryl-1-haloindolizines from Pyridinium Salts and 2-Aryl-1,1-dihaloalk-1-enes

Yiwen Yanga,b, Chunxiang Kuang*a, Hui Jina, Qing Yang*c
a Department of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China
Fax: +86(21)65983191; e-Mail: kuangcx@tongji.edu.cn;
b School of Biology and Chemical Engineering, Jiaxing University, Jiaxing 314001, P. R. of China
c Department of Biochemistry, School of Life Sciences, Fudan University, Handan Road 220, Shanghai 200433, P. R. of China
e-Mail: yangqing68@fudan.edu.cn;
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Publication History

Received 7 July 2011
Publication Date:
07 September 2011 (online)

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Abstract

2-Aryl-1-haloindolizines were synthesized from pyridinium salts and 2-aryl-1,1-dihaloalk-1-enes using a DBU/THF system. 2-Aryl-1,1-dihaloalk-1-enes containing electron-withdrawing or -donating groups were efficiently converted into the corresponding 2-aryl-1-haloindolizines in moderate to excellent yields.

Key words

2-aryl-1-haloindolizines - pyridinium - 1,1-dihaloalk-1-enes - haloalkyne - 1,3-dipolar cycloaddition