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One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation
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2013
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New ApplicationDiversity Oriented SynthesisDerivativesEngineeringBiochemistryNatural SciencesDiversity-oriented SynthesisOne-pot SynthesisOrganic ChemistryCatalysisPhenyliodine DiacetateChemistryHeterocycle ChemistryNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringMild Reaction Conditions
A variety of 4(3<i>H</i>)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by <i>p</i>-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)<sub>2</sub>, PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an <i>N</i>-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions.