Highly efficient synthesis of polysubstituted pyrroles via four-component domino reaction

Xian Feng; Qian Wang; Wei Lin; Guo-Lan Dou; Zhi-Bin Huang; Da-Qing Shi

doi:10.1021/ol4010382

Highly efficient synthesis of polysubstituted pyrroles via four-component domino reaction

Org Lett. 2013 May 17;15(10):2542-5. doi: 10.1021/ol4010382. Epub 2013 May 1.

Authors

Xian Feng¹, Qian Wang, Wei Lin, Guo-Lan Dou, Zhi-Bin Huang, Da-Qing Shi

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, P. R. China, and School of Safety Engineering, China University of Mining & Technology , Xuzhou 221116, P. R. China.

PMID: 24490761
DOI: 10.1021/ol4010382

Abstract

A highly efficient, catalyst-free synthesis of polysubstituted pyrroles by means of a novel four-component domino reaction of an arylglyoxal monohydrate, an aniline, a dialkyl but-2-ynedioate, and malononitrile is reported. This transformation proceeded via a 6,6a-dihydrofuro[2,3-b]pyrrole as the key intermediate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemistry
Catalysis
Molecular Structure
Nitriles / chemistry
Pyrroles / chemical synthesis*
Pyrroles / chemistry

Substances

6,6a-dihydrofuro(2,3-b)pyrrole
Aniline Compounds
Nitriles
Pyrroles
dicyanmethane
aniline