Synthesis of 4-Aryl Isoquinolinedione Derivatives by a Palladium-Catalyzed Coupling Reaction of Aryl Halides with Isoquinoline-1,3(2 H,4 H)-diones

Yuanyong Yang; Yingxian Li; Cheng Cheng; Guo Yang; Jiquan Zhang; Yi Zhang; Yonglong Zhao; Lin Zhang; Chun Li; Lei Tang

doi:10.1021/acs.joc.7b02961

Synthesis of 4-Aryl Isoquinolinedione Derivatives by a Palladium-Catalyzed Coupling Reaction of Aryl Halides with Isoquinoline-1,3(2 H,4 H)-diones

J Org Chem. 2018 Mar 16;83(6):3348-3353. doi: 10.1021/acs.joc.7b02961. Epub 2018 Feb 23.

Authors

Yuanyong Yang^{1

2}, Yingxian Li¹, Cheng Cheng¹, Guo Yang¹, Jiquan Zhang^{1

2}, Yi Zhang^{1

2}, Yonglong Zhao^{1

2}, Lin Zhang^{1

2}, Chun Li^{1

2}, Lei Tang^{2

3}

Affiliations

¹ School of Pharmacy , Guizhou Medical University , Guiyang 550004 , China.
² State Key Laboratory of Functions and Applications of Medicinal Plants , Guizhou Medical University , Guiyang 550014 , China.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica , Chinese Academy of Sciences , Shanghai 201203 , China.

PMID: 29400968
DOI: 10.1021/acs.joc.7b02961

Abstract

The palladium-catalyzed cross-coupling reaction of aryl halides with isoquinoline-1,3(2 H,4 H)-diones for the synthesis of 4-aryl isoquinoline-1,3(2 H,4 H)-diones was developed. The reaction conditions exhibit remarkable compatibility with various aryl halides and isoquinoline-1,3(2 H,4 H)-diones, and the product could be conveniently transformed to 4-aryl tetrahydroisoquinolines. (±) Dichlorofensine was synthesized using this protocol in two steps with an overall yield of 71%.

Publication types

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