Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generated in situ via C=C bond cleavage

• Published in: Organic & biomolecular chemistry Vol. 19; no. 11; pp. 2436 - 2441
• Main Authors: Xie, Zongbo, Lan, Jin, Yan, Liyuan, Chen, Xuehua, Li, Qian, Meng, Jia, Le, Zhanggao
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.03.2021; Royal Society of Chemistry
• Subjects: Aldehydes; Aniline; Chemistry; Chemistry, Organic; Cleavage; Dehydrogenation; Oxidants; Oxidation; Oxidizing agents; Oxygen; Photocatalysts; Physical Sciences; Quinazolinone; Quinazolinones; Room temperature; Science & Technology; Styrene; Volatilization; 2,3-DIHYDROQUINAZOLIN-4(1H)-ONES; OXIDATION; ALKENES; DESIGN; OZONOLYSIS; FACILE; EFFICIENT; DERIVATIVES; CYCLIZATION; MOLECULAR-OXYGEN
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d0ob02268c

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides and in situ-generated aldehydes. The latter was formed via C=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with an o-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.