Visible light-promoted synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones via a tandem radical cyclization and sulfonylation reaction

Xu Liu; Tiantian Cong; Ping Liu; Peipei Sun

doi:10.1039/c6ob01569g

Visible light-promoted synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones via a tandem radical cyclization and sulfonylation reaction

Org Biomol Chem. 2016 Oct 4;14(39):9416-9422. doi: 10.1039/c6ob01569g.

Authors

Xu Liu¹, Tiantian Cong¹, Ping Liu¹, Peipei Sun¹

Affiliation

¹ College of Chemistry and Materials Science, Nanjing Normal University; Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control; Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing 210023, China. sunpeipei@njnu.edu.cn.

PMID: 27714231
DOI: 10.1039/c6ob01569g

Abstract

Heterocyclic derivatives 4-(sulfonylmethyl)isoquinoline-1,3(2H,4H)-diones were synthesized via a visible-light-promoted reaction of N-alkyl-N-methacryloyl benzamides with sulfonyl chlorides catalyzed by fac-Ir(ppy)₃ at room temperature. With various substituents on the substrates, the reaction proceeded smoothly to give the corresponding products in good to excellent yields. The products could be converted into 3-hydroxy-4-(sulfonylmethyl)-3,4-dihydroisoquinolin-1(2H)-one derivatives by the reduction of NaBH₄.