Publication: Synthesis of 4-Tetrazolyl-Substituted 3,4-Dihydroquinazoline Derivatives with Anticancer Activity via a One-Pot Sequential Ugi-Azide/Palladium-Catalyzed Azide-Isocyanide Cross-Coupling/Cyclization Reaction.

Publié dans: J Org Chem 2022 Aug; 87(15): 9488-9496

Auteurs: Xiong J, He HT, Yang HY, Zeng ZG, Zhong CR, Shi H, Ouyang ML, Tao YY, Pang YL, Zhang YH, Hu B, Fu ZX, Miao XL, Zhu HL, Yao G

Résumé

A new one-pot preparation of 4-tetrazolyl-3,4-dihydroquinazolines has been reported. The Ugi-azide reactions of 2-azidobenzaldehydes, amines, trimethylsilyl azide, and isocyanides produced azide intermediates without separation, which were treated with isocyanides to give 4-tetrazolyl-3,4-dihydroquinazoline derivatives through a sequential Palladium-catalyzed azide-isocyanide cross-coupling/cyclization reaction in moderate to good yields. The biological evaluation demonstrated that compound 6c inhibited breast cancer cells well and displayed broad applications for synthesis and medicinal chemistry.

Lien vers Pubmed [PMID] – 35881945

Lien vers le DOI – 10.1021/acs.joc.2c00382