Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N-(2-Furanylmethyl) Alkynamides under Air

Yongjie Yang; ChengCheng Fei; Kai Wang; Bo Liu; Dingxin Jiang; Biaolin Yin

doi:10.1021/acs.orglett.8b00618

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N-(2-Furanylmethyl) Alkynamides under Air

Org Lett. 2018 Apr 20;20(8):2273-2277. doi: 10.1021/acs.orglett.8b00618. Epub 2018 Apr 9.

Authors

Yongjie Yang¹, ChengCheng Fei², Kai Wang³, Bo Liu³, Dingxin Jiang², Biaolin Yin¹

Affiliations

¹ Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510640 , P. R. China.
² Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, Laboratory of Insect Toxicology , South China Agricultural University , Guangzhou 510642 , P. R. China.
³ Guangdong Provincial Academy of Chinese Medical Sciences , Guangzhou 510006 , P. R. China.

PMID: 29630382
DOI: 10.1021/acs.orglett.8b00618

Abstract

A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.

Publication types

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