2. Academic Validation
  3. 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

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

  • J Org Chem. 2022 Aug 5;87(15):9488-9496. doi: 10.1021/acs.joc.2c00382.
Jun Xiong 1,  Hui-Ting He 1,  He-Yu Yang 1,  Zhi-Gang Zeng 2,  Cheng-Ran Zhong 1,  Hang Shi 1,  Meng-Ling Ouyang 1,  Yuan-Yuan Tao 1,  Yong-Long Pang 1,  Yang-Hong Zhang 1,  Bo Hu 1,  Zi-Xiang Fu 1,  Xiao-Lei Miao 1,  Hai-Li Zhu 3,  Gang Yao 1
Affiliations

Affiliations

  • 1 School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, Hubei, P. R. China.
  • 2 School of Nuclear Technology and Chemistry & Biology, Hubei University of Science and Technology, Xianning 437100, P. R. China.
  • 3 School of Basic Medical Sciences, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, P. R. China.
PMID: 35881945 DOI: 10.1021/acs.joc.2c00382
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.

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