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

Frontiers in Chemistry (May 2022)

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

Affiliations

Shanqing Tao: Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China
Aiwen Huo: Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao, China
Yan Gao: Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China
Xiangyang Zhang: Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China
Jingyue Yang: Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao, China
Yunfei Du: Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China

DOI: https://doi.org/10.3389/fchem.2022.859995
Journal volume & issue: Vol. 10

Abstract

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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.

Published in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

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