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One-Pot Oxidative Coupling/Decyanation of 6,7-Diphenylindolizine-5-carbonitriles and 2,3-Diphenylquinolizine-4-carbonitriles.

Yi-Hsuan ChenRong-Shiow TangLi-Yuan ChenTa-Hsien Chuang
Published in: The Journal of organic chemistry (2019)
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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