Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 14-15, Pages 3148-3156Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400420
Keywords
aerobic oxidative cyclization; azaspirocyclohexadienones; alpha-azido-N-phenylacetamides; tert-butyl hydroperoxide; iminyl radicals; tetrabutylammonium iodide
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Funding
- National Natural Science Foundation of China [21372108]
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The oxidizing system of tert-butyl hydroperoxide (TBHP) and tetrabutylammonium iodide (TBAI) is capable of engendering alpha-(aminocarbonyl)iminyl radicals from alpha-azido-N-phenylacetamides. These iminyl radicals preferably undergo intramolecular attack on the benzene ring to give azaspirocyclohexadienyl radicals, which are readily captured by O-2 under an oxygen atmosphere to yield azaspirocyclohexadienones. In the absence of oxygen, the reaction will afford quinoxalin-2-one products. The generation of alpha-(aminocarbonyl) iminyl radicals is proposed to involve an initial deprotonation and denitrogenation, and subsequent oxidation of thus formed imine intermediates by tert-butoxy radical and/or tert-butyl peroxyl radical.
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