One-Pot Oxidative Coupling/Decyanation of 6,7-Diphenylindolizine-5-carbonitriles and 2,3-Diphenylquinolizine-4-carbonitriles
2019
Chen, Yi-Hsuan | Tang, Rong-Shiow | Chen, Li-Yuan | Chuang, Ta-Hsien
The one-pot oxidative coupling/decyanation reactions of 6,7-diphenylindolizine-5-carbonitriles and 2,3-diphenylquinolizine-4-carbonitriles were investigated using aryl–aryl oxidative coupling reagents. The phenanthroindolizidinones and phenanthroquinolizidinones were produced in 52–89% yields under VOF₃/trifluoroacetic acid or [bis(trifluoroacetoxy)iodo]benzene/BF₃-mediated conditions. This represents a mild and efficient approach to construct these types of pentacyclic skeletons from the corresponding cyano group-activated aza-Diels–Alder cycloadducts. A plausible mechanism of the one-pot oxidative coupling/decyanation reaction was proposed.
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