Synthesis 2017; 49(10): 2241-2249
DOI: 10.1055/s-0036-1588717
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Polyfunctionalized Pyrroles from Furfurylamines and Ynones via CuCl2-Catalyzed and Iodine-Mediated Oxidative Annulation of N-Furfuryl-β-Enaminones

Jie Zou
a   State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, P. R. of China   eMail: rdyang@scut.edu.cn
,
Guohui Zeng
b   Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. of China   eMail: blyin@scut.edu.cn
,
Rendang Yang*
a   State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, P. R. of China   eMail: rdyang@scut.edu.cn
,
Biaolin Yin*
b   Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. of China   eMail: blyin@scut.edu.cn
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Publikationsverlauf

Received: 05. Januar 2017

Accepted after revision: 23. Januar 2017

Publikationsdatum:
16. Februar 2017 (online)


Abstract

The copper chloride catalyzed and iodine-mediated oxidative annulation of N-furfuryl-β-enaminones, generated in situ from reactions of furfurylamines with ynones, provides a practical access to polyfunctionalized pyrroles under mild conditions. This protocol expands the synthetic application of furans, which are readily available and can be sustainably sourced.

Supporting Information