Affiliation:
1. Anhui Key Laboratory of Low Temperature Co-Fired Materials, School of Chemistry and Material Engineering, Huainan Normal University, Huainan 232038, China
2. School of Pharmacy, Xianning Medical College, Hubei University of Science and Technology, Xianning 437100, China
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 the direct functionalization of sp3 C-H bonds adjacent to the nitrogen atom. This method offered several notable advantages, including ligands-free, exceptional productivity and a 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.
Funder
Hubei Provincial Natural Science Foundation of China
Science and Technology Plan Project of Huainan City
Doctoral Foundation of Huainan Normal University
Medical Research Project of Hubei University of Science and Technology
Hubei University of Science and Technology Doctoral Research Initiation Project
Innovation and Entrepreneurship training Program for College students of Hubei University of Science and Technology
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