Substituent-controlled chemoselective synthesis of multi-substituted pyridones via a one-pot three-component cascade reaction

Shitao Liu; Jisen Li; Junjie Lin; Fujun Liu; Teng Liu; Chao Huang

doi:10.1039/c9ob02456e

Substituent-controlled chemoselective synthesis of multi-substituted pyridones via a one-pot three-component cascade reaction

Org Biomol Chem. 2020 Feb 14;18(6):1130-1134. doi: 10.1039/c9ob02456e. Epub 2020 Jan 20.

Authors

Shitao Liu¹, Jisen Li¹, Junjie Lin¹, Fujun Liu¹, Teng Liu², Chao Huang¹

Affiliations

¹ National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. China. huangchao@ynu.edu.cn.
² Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control, Qujing Normal University, Qujing, 655011, P. R. China. 15288404381@163.com.

PMID: 31956881
DOI: 10.1039/c9ob02456e

Abstract

An efficient and concise one-pot strategy for the synthesis of multisubstituted pyridones via a one-pot three-component cascade reaction catalyzed by Cs₂CO₃ under solvent-free conditions has been developed. The substituent-controlled chemoselective cycloaddition process involved steps including a Michael addition/ethanol elimination/intermolecular cyclization sequence utilizing anilines, diethyl acetylenedicarboxylate, and diethyl ethoxymethylenemalonate. In doing so, various 2-pyridone and 4-pyridone species (41 examples) could be obtained in good to excellent yields.

Publication types

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