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
Jun Xiong, Huiting He, He‐Yu Yang, Zhigang Zeng, Cheng‐Ran Zhong, Hang Shi, Meng-Ling Ouyang, Yuanyuan Tao, Yong‐Long Pang, Yang-Hong Zhang, Bo Hu, Zi-Xiang Fu, Xiaolei Miao, Haili Zhu, Gang Yao
Abstract
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.