Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5H-Quinazolino[3,2-a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization

2023/01/17 by Mao-Lin Yang, Long Zhao, Hao Chen +3 · 5 citations
Chemistry · #Quinazolinone synthesis and applications #Multicomponent Synthesis of Heterocycles #Synthesis and Characterization of Heterocyclic Compounds

paper · doi:10.1021/acs.joc.2c02621

Abstract

A new efficient and stereoselective synthesis of 12-tetrazolyl substituted ( E )-5 H -quinazolino[3,2- a ]quinazolines via sequential Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed cyclization was developed. The four-component reactions of 2-azidobenzaldehyde, 2-(alkynyl)benzenamine, isocyanide, and trimethylsilyl azide gave Ugi-azide intermediates, which were subsequently treated with triphenylphosphine and isocyanate to produce 12-tetrazolyl substituted ( E )-5 H -quinazolino[3,2- a ]quinazolines in the presence of Ag(I) catalyst and K 2 CO 3 .

Citations

• 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

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