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

• Published in: Journal of organic chemistry Vol. 77; no. 16; pp. 7046 - 7051
• Main Authors: Hikawa, Hidemasa, Ino, Yukari, Suzuki, Hideharu, Yokoyama, Yuusaku
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.08.2012; Amer Chemical Soc
• Subjects: Benzamides - chemistry; Benzyl Alcohols - chemistry; Carbon - chemistry; Catalysis; Chemistry; Chemistry, Organic; 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; Physical Sciences; Preparations and properties; Quinazolinones - chemical synthesis; Science & Technology; Stereoisomerism; Water; SYSTEM; CARBONYLATION; ONE-POT SYNTHESIS; RECEPTOR; 4(3H)-QUINAZOLINONES; DERIVATIVES; EFFICIENT; DRY MEDIA; CYCLIZATION; CONVERSIONS; Water; Benzylation; Catalytic reaction; Nitrogen heterocycle; Quinazoline derivatives; Palladium complex; Transition metal; Activation; Palladium; Benzyl alcohol; Amidation; Benzylic compound; Dehydrogenation; Hydroxyl group; Benzenic compound; Benzamide derivatives; Chemical synthesis; Platinoid; Successive reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo301282n

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.