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
Abstract
The application of PhICl 2 /NH 4 SCN and PhICl 2 /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.
Topics & Concepts
IsocoumarinsChemistryThio-RegioselectivityElectrophileReagentCombinatorial chemistryDerivatizationOrganic chemistryCatalysisHigh-performance liquid chromatographySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistrySynthesis and Catalytic Reactions