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Application of novel nanostructured dinitropyrazine molten salt catalyst for the synthesis of sulfanylpyridines via anomeric based oxidation

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Abstract

1,4-Dinitropyrazine-1,4-diium trinitromethanide {[1,4-pyrazine-NO2][C(NO2)3]2} as a novel nanostructured molten salt (NMS) catalyzed the synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridine derivatives via the one-pot three-component condensation reaction between several aromatic aldehyde, malononitrile and benzyl mercaptan at room temperature under solvent-free conditions. The synthesized NMS catalyst was fully characterized by FTIR, 1H NMR, 13CNMR, mass, thermal gravimetric, X-ray diffraction patterns, scanning electron microscopy and transmission electron microscopy analysis. The major advantages of described methodology are mildness, ease of separation, good yields and short reaction times. A rational mechanism was suggested for the final step of the 2-amino-3,5-dicarbonitrile-6-sulfanylpyridines synthesis. We think that the proposed mechanism has potential for entering into the graduate text book in the future.

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Acknowledgements

We thank Bu-Ali Sina University, Iran National Science Foundation (INSF, Grant No: 95831207) and National Elites Foundation for financial support to our research group.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Mohammad Ali Zolfigol, Bahar Ebrahimghasri, Saeed Baghery, Saied Alaie & Mahya Kiafar

  2. Department of Medicinal Plants Production, Nahavand University, Nahavand, 6593139565, Iran

    Maliheh Safaiee

  3. Department of Organic Chemistry, Razi University, P.O. Box: 67149-67346, Kermanshah, Iran

    Avat Taherpour

  4. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Avat Taherpour

  5. Faculty of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran

    Yadollah Bayat & Asiye Asgari

Authors
  1. Mohammad Ali Zolfigol
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  2. Maliheh Safaiee
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  3. Bahar Ebrahimghasri
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Correspondence to Mohammad Ali Zolfigol or Maliheh Safaiee.

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Zolfigol, M.A., Safaiee, M., Ebrahimghasri, B. et al. Application of novel nanostructured dinitropyrazine molten salt catalyst for the synthesis of sulfanylpyridines via anomeric based oxidation. J IRAN CHEM SOC 14, 1839–1852 (2017). https://doi.org/10.1007/s13738-017-1123-z

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