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Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins

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Abstract

5-Arylidene-1-methyl-2-thiohydantoins undergo [3+2]-cycloaddition reaction with nitrile imines, generated in situ from hydrazonyl chlorides, at C=C and C=S dipolarophiles in the thiohydantoin moiety to afford thioxo-tetraazaspiro[4.4]nonenones and thia-tetraazaspiro[4.4]nonenones in moderate to good yields. The stereochemistry of these spiroheterocycles has been confirmed by X-ray diffraction studies.

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Acknowledgements

We 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, P.O. Box 14115-175, Tehran, Iran

    Issa Yavari, Zohreh Taheri & Sara Sheikhi

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

    Samira Bahemmat & Mohammad R. Halvagar

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  1. Issa Yavari
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  2. Zohreh Taheri
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  3. Sara Sheikhi
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Correspondence to Issa Yavari.

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Yavari, I., Taheri, Z., Sheikhi, S. et al. Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins. Mol Divers 25, 777–785 (2021). https://doi.org/10.1007/s11030-020-10056-8

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