 |
| PAPER | Synthesis 2004: 1951-1954
DOI: 10.1055/s-2004-829182 |
© Georg Thieme Verlag Stuttgart · New York
|
 |
Organic Reactions in Ionic Liquids: A Simple and Highly Regioselective N-Substitution of Pyrrole
|
| Zhang-Gao Lea,b,c, Zhen-Chu Chen*a,b, Yi Hub, Qin-Guo Zhengd |
a Ningbo Institute of Technology, Zhejiang University, Ningbo, 315100, P. R. China
b Department of Chemistry, Zhejiang University (xi xi campus), Hangzhou, 310028, P. R. China
e-Mail: zhenchuc@mail.hz.zj.cn;
c Department of Applied Chemistry, East China Institute of Technology, Fuzhou, 344000, P. R. China
d Pharmaceutical Science Reseach Institute, Aston University, Aston Triangle, Birmingham B4 TET, UK
|
|
Received
25 March 2004 |
Abstract
In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles. Key words
pyrroles - substitution - ionic liquids - alkylation - sulfonylation - acylation
| |
