Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generated in situ via C[double bond, length as m-dash]C bond cleavage.


Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
21 Mar 2021
Historique:
pubmed: 7 1 2021
medline: 7 1 2021
entrez: 6 1 2021
Statut: ppublish

Résumé

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[double bond, length as m-dash]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.

Identifiants

pubmed: 33406170
doi: 10.1039/d0ob02268c
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2436-2441

Auteurs

Zongbo Xie (Z)

Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013, China. zbxie@ecut.edu.cn zhgle@ecut.edu.cn.

Classifications MeSH