Pd-Catalyzed Benzylic C–H Amidation with Benzyl Alcohols in Water: A Strategy To Construct Quinazolinones

A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C–H amidation, and dehydrogenation in water, which may play an important role in the smooth gene...

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Veröffentlicht in:	Journal of organic chemistry 2012-08, Vol.77 (16), p.7046-7051
Hauptverfasser:	Hikawa, Hidemasa, Ino, Yukari, Suzuki, Hideharu, Yokoyama, Yuusaku
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzamides - chemistry Benzyl Alcohols - chemistry Carbon - chemistry Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Hydrogen - chemistry Magnetic Resonance Spectroscopy Molecular Structure Noncondensed benzenic compounds Organic chemistry Palladium - chemistry Preparations and properties Quinazolinones - chemical synthesis Stereoisomerism Water
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Beschreibung
Zusammenfassung:	A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C–H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo301282n