Ag2O mediated N-demethylation and oxidative opening of indenopyrido[2,1-a]isoindolones. Efficient access to polysubstituted 1-azafluorenones?

RSC Advances Pub Date: 2013-08-07 DOI: 10.1039/C3RA43278E

Abstract

Highly functionalized 1-azafluorenones were obtained from indeno[2,1-a]isoindolones through Ag2O-mediated cascade reaction. The cascade process includes the oxidation of vicinal alcohol and dihydropyridine to generate a pyridinium intermediate which is trapped in situ by a nucleophile. Functional groups such as methoxy, thiomethyl and aldehyde survived the Ag2O treatment whereas the dimethylamino group was partially demethylated.

Graphical abstract: Ag2O mediated N-demethylation and oxidative opening of indenopyrido[2,1-a]isoindolones. Efficient access to polysubstituted 1-azafluorenones
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