PhICl2-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins

Shanqing Tao; Aiwen Huo; Yan Gao; Xiangyang Zhang; Jingyue Yang; Yunfei Du

doi:10.3389/fchem.2022.859995

PhICl₂-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins

Front Chem. 2022 May 18:10:859995. doi: 10.3389/fchem.2022.859995. eCollection 2022.

Authors

Shanqing Tao¹, Aiwen Huo², Yan Gao¹, Xiangyang Zhang¹, Jingyue Yang², Yunfei Du¹

Affiliations

¹ Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China.
² Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao, China.

Abstract

The application of PhICl₂/NH₄SCN and PhICl₂/KSeCN reagent systems to the synthesis of the biologically active S/SeCN-containing isocoumarins via a process involving thio/selenocyanation, enabled by thio/selenocyanogen chloride generated in situ, followed with an intramolecular lactonization was realized. Gram-scale synthesis, further derivatization to access C4 thio/selenocyanated Xyridin A and anti-tumor activities of the obtained products highlight the potential use of this method.

Keywords: PhICl2; isocoumarin; o-(1-Alkynyl)benzoate; oxyselenocyanation; oxythiocyanation.