Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide Double Insertion Reaction with Terminal Alkynes and Water

Yan He; Ying-Chun Wang; Kun Hu; Xiao-Ling Xu; Heng-Shan Wang; Ying-Ming Pan

doi:10.1021/acs.joc.6b02288

Palladium-Catalyzed Synthesis of 5-Iminopyrrolones through Isocyanide Double Insertion Reaction with Terminal Alkynes and Water

J Org Chem. 2016 Dec 2;81(23):11813-11818. doi: 10.1021/acs.joc.6b02288. Epub 2016 Nov 9.

Authors

Yan He¹, Ying-Chun Wang², Kun Hu¹, Xiao-Ling Xu¹, Heng-Shan Wang¹, Ying-Ming Pan¹

Affiliations

¹ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University , Guilin 541004, People's Republic of China.
² College of Chemistry and Chemical Engineering, Jishou University , Jishou 416000, People's Republic of China.

PMID: 27805820
DOI: 10.1021/acs.joc.6b02288

Abstract

With the combination of Pd(dppf)Cl₂ and Cu(OAc)₂, a variety of 5-iminopyrrolones were synthesized in moderate to good yields from terminal alkynes, isocyanide, and water via isocyanide double insertion and cycloaddition reaction. A plausible reaction mechanism for this process is depicted. Furthermore, selected compounds 3c, 3e, and 3h exhibited good activities against HepG2 (human liver cancer), NCI-H460 (human lung cancer), and SK-OV-3 (human ovarian cancer) cell lines with IC₅₀ values in the range of 10.63-22.63 μmol L^-1.

Publication types

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