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J Org Chem. 2019 Apr 5;84(7):4501-4506. doi: 10.1021/acs.joc.9b00041. Epub 2019 Mar 21.

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

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1
School of Pharmacy , China Medical University , Taichung 40402 , Taiwan.

Abstract

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.

PMID:
30864446
DOI:
10.1021/acs.joc.9b00041

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