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One-step Construction of 1,3,4-oxadiazoles from Tertiary Amines via a Sequential Copper(I)-Catalyzed Oxidative Ugi/aza-Wittig Reaction
  • +8
  • Mei Sun,
  • Nong-Qi Mao,
  • Sheng-Long Wang,
  • Xin-Ming Han,
  • Gang Yao,
  • Ping Xue,
  • Chong-Yang Zeng,
  • Yu-Ting Liu,
  • Kai Chen,
  • Gao Xiao-Qing,
  • Jun Xiong
Mei Sun
Huainan Normal University
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Nong-Qi Mao
Hubei University of Science and Technology
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Sheng-Long Wang
Hubei University of Science and Technology
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Xin-Ming Han
Hubei University of Science and Technology
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Gang Yao
Hubei University of Science and Technology
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Ping Xue
Hubei University of Science and Technology
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Chong-Yang Zeng
Huainan Normal University
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Yu-Ting Liu
Huainan Normal University
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Kai Chen
Huainan Normal University
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Gao Xiao-Qing
Huainan Normal University
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Jun Xiong
Hubei University of Science and Technology

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Abstract

An unparalleled copper(I)-catalyzed synthesis of 1,3,4-oxadiazoles from tertiary amines in one step has been described. The one-pot reactions involving (N-isocyanimine)triphenylphosphorane , tertiary amines , and carboxylic acids resulted in the formation of 1,3,4-oxadiazoles in moderate to good yields through a consecutive oxidative Ugi/aza-Wittig reaction, enabling direct functionalization of sp3 C-H bonds adjacent to the nitrogen atom. This method offered several notable advantages, including mild reaction conditions, ligands free, exceptional productivity and high functional group tolerance. The preliminary biological evaluation demonstrated that compound 4f inhibited hepatoma cells efficiently, suggesting potentially broad applications of the approach for synthesis and medicinal chemistry.