Silver-Catalyzed Cascade Reaction of β-Enaminones and Isocyanoacetates To Construct Functionalized Pyrroles

Guichun Fang; Jianquan Liu; Junkai Fu; Qun Liu; Xihe Bi

doi:10.1021/acs.orglett.7b00201

Silver-Catalyzed Cascade Reaction of β-Enaminones and Isocyanoacetates To Construct Functionalized Pyrroles

Org Lett. 2017 Mar 17;19(6):1346-1349. doi: 10.1021/acs.orglett.7b00201. Epub 2017 Feb 28.

Authors

Guichun Fang¹, Jianquan Liu^{1

2}, Junkai Fu¹, Qun Liu¹, Xihe Bi^{1

3}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.
² School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University , Xuzhou 221116, China.
³ State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.

PMID: 28244762
DOI: 10.1021/acs.orglett.7b00201

Abstract

An unexpected silver-catalyzed cascade reaction of β-enaminones and isocyanoacetates affording functionalized pyrrole derivatives is reported. In this reaction, tautomeric equilibria of β-enaminones are utilized to generate imine partners in situ. A hypothesized sequential Mannich addition/cyclization of imine tautomers and isocyanoacetates followed by an unprecedented ring-opening of the resultant 2-imidazolines and dehydration-condensation deliver the final 1,2,4,5-tetrasubstituted pyrrole products.

Publication types

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