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One-Step Construction of 1,3,4-Oxadiazoles with Anticancer Activity from Tertiary Amines via a Sequential Copper(I)-Catalyzed Oxidative Ugi/aza-Wittig Reaction.

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.

SUBMITTER: Sun M 

PROVIDER: S-EPMC10975333 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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One-Step Construction of 1,3,4-Oxadiazoles with Anticancer Activity from Tertiary Amines via a Sequential Copper(I)-Catalyzed Oxidative Ugi/aza-Wittig Reaction.

Sun Mei M   Mao Nong-Qi NQ   Wang Sheng-Long SL   Han Xin-Ming XM   Yao Gang G   Xue Ping P   Zeng Chong-Yang CY   Liu Yu-Ting YT   Chen Kai K   Gao Xiao-Qing XQ   Xiong Jun J  

Molecules (Basel, Switzerland) 20240312 6

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 sp<sup>3</sup> C-H bonds adjacent to the nitrogen atom. This method offered several notable advantag  ...[more]

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