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One-pot carbonylation-dehydration tandem reaction of aryl iodides with acylhydrazines for synthesis of 2,5-diaryl-1,3,4-oxadiazoles

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Abstract

The structures of 2,5-diaryl-1,3,4-oxadiazoles with good stability have attract great attention for development of new and safe therapeutic agents with functions in antimicrobial, anti-inflammatory, antitumor, and antiviral (for treatment of HIV infection), etc. In the present work, over the developed Pd-catalytic system with involvement of the 3-thiophenyl-benzimidazolyl-based mono-phosphine, the one-pot carbonylation-dehydration tandem reaction of aryl iodides with acylhydrazines for synthesis of 2,5-diaryl-1,3,4-oxadiazoles was reported for the first time with advantages of simplified manipulations, high efficiency (yields of 62–93%), as well as high safety of applied organic substrates. The relatively high reaction temperature of 140–160 ℃ was required for this tandem reaction, wherein the good stability of the involved phosphine with suitable stereo-electronic property guaranteed the fulfilment of this sequence. It was demonstrated that the first-step carbonylation of aryl iodides with acylhydrazine toward N,N′-diarylhydrazides was the rate-determine step in the overall process. Subsequently, the formed N,N'-dibenzoylhydrazides irreversible dehydrated into 2,5-diaryl-1,3,4-oxadiazoles with the presence of dehydrating agent like DCC.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 22172052 and 21972045), and the Research Funds of Happiness Flower ECNU (2022ST2203).

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Authors and Affiliations

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, People’s Republic of China

    Lin Guo, Shu-Qing Yang, Kai-Chun Zhao, Xiao-Chao Chen, Yong Lu & Ye Liu

  2. Institute of Eco-Chongming (IEC), East China Normal University, Shanghai, 202162, People’s Republic of China

    Yong Lu & Ye Liu

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  1. Lin Guo
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  2. Shu-Qing Yang
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  3. Kai-Chun Zhao
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  4. Xiao-Chao Chen
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  5. Yong Lu
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  6. Ye Liu
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Correspondence to Ye Liu.

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Guo, L., Yang, SQ., Zhao, KC. et al. One-pot carbonylation-dehydration tandem reaction of aryl iodides with acylhydrazines for synthesis of 2,5-diaryl-1,3,4-oxadiazoles. Monatsh Chem 154, 215–222 (2023). https://doi.org/10.1007/s00706-022-03021-8

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  • DOI: https://doi.org/10.1007/s00706-022-03021-8

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