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Paper | Regular issue | Vol 100, No. 5, 2020, pp.768-780
Published online, 1st April, 2020
DOI: 10.3987/COM-20-14243
Regioselective Synthesis of Quinoxalin-2-one Derivatives Regulated by Acid and Base

Wanli Liu, Qifeng Su, Kang Qiu, Meng Wang,* and Qun Lu*

*School of Life Science and Engineering, Southwest Jiaotong University, NO.111, North Second Ring Road Chengdu 610031, Sichuan, China

Abstract

A concise approach for the synthesis of quinoxalin-2-one derivatives through substituted o-phenylenediamines and α-ketoester with high regioselectivity is developed. Interestingly, the two regioisomers can be selectively obtained and the regioselectivity can be regulated by acid and base. The typical regioisomer ratio is up to 15:1 in acidic conditions and it can be easily reversed as 1:4 in basic conditions.