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Synthesis 2012(4): 532-540  
DOI: 10.1055/s-0031-1289993
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrasubstituted NH Pyrroles and Polysubstituted Furans via an Addition and Cyclization Strategy

Liang Li, Mi-Na Zhao, Zhi-Hui Ren, Jianli Li, Zheng-Hui Guan*
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China
e-Mail: guanzhh@nwu.edu.cn;
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Publikationsverlauf

Received 5 October 2011
Publikationsdatum:
22. Dezember 2011 (online)

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Abstract

The FeCl3-catalyzed addition and cyclization of enamino esters with nitroolefins provides a straightforward and general method for the synthesis of tetrasubstituted NH pyrroles. This novel method tolerates a wide range of functionality, and allows for rapid elaboration of the nitroolefins into a variety of substituted pyrroles in good yields. Further, an efficient KOAc-promoted addition and cyclization protocol toward substituted furans has been described as well.

Key words

tetrasubstituted NH pyrroles - polysubstituted furans - addition - cyclization