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

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.
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https://hal.univ-lorraine.fr/hal-01494612
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Submitted on : Thursday, March 23, 2017 - 4:56:04 PM
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Victor Mamane, Zein El Abidine Chamas, Emmanuel Aubert, Yves Fort. Ag2O mediated N-demethylation and oxidative opening of indenopyrido[2,1-a]isoindolones. Efficient access to polysubstituted 1-azafluorenones . RSC Advances, Royal Society of Chemistry, 2013, 41 (3), pp.19110-19116 ⟨10.1039/C3RA43278E⟩. ⟨hal-01494612⟩

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