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A diastereoselective synthesis of functionalized spiropyrrolizidine-linked rhodanines

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Abstract

A diastereoselective practical route to functionalized spiropyrrolizidine-linked rhodanines has been developed via 1,3-dipolar cycloaddition reaction of alkylidenerhodanines with azomethine ylides, prepared in situ from l-proline and acetylenic esters, in EtOH at reflux. This protocol provided quick access to a range of structurally diverse target molecules in moderate-to-good yields. The structure of a typical product was established by X-ray crystallography.

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Acknowledgements

We would like to thank the Research Council of Tarbiat Modares University for supporting this work.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran

    Issa Yavari, Sara Sheikhi & Zohreh Taheri

  2. Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran

    Mohammad Reza Halvagar

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  1. Issa Yavari
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  2. Sara Sheikhi
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  3. Zohreh Taheri
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  4. Mohammad Reza Halvagar
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Correspondence to Issa Yavari.

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Yavari, I., Sheikhi, S., Taheri, Z. et al. A diastereoselective synthesis of functionalized spiropyrrolizidine-linked rhodanines. Monatsh Chem 150, 1825–1831 (2019). https://doi.org/10.1007/s00706-019-02485-5

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  • DOI: https://doi.org/10.1007/s00706-019-02485-5

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