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Green synthesis of indol-2-one derivatives from N-alkylisatins in the presence of KF/clinoptilolite nanoparticles

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Chemistry of Heterocyclic Compounds Aims and scope

KF/clinoptilolite nanoparticles were used as an effective heterogeneous catalyst for the synthesis of spiro[indole-3,2'-pyran] derivatives via three-component reactions of N-alkylisatins, 1,3-dicarbonyl compounds, and electron-deficient acetylenic compounds under solventfree conditions at 80°C. The present protocol has significant advantages, such as high yields, easy purification, and low environmental impact.

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References

  1. Li, C.-J.; Chan, T.-H. Comprehensive Organic Reactions in Aqueous Media; John Wiley & Sons, 2007, 2nd ed.

  2. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.

    Article  CAS  Google Scholar 

  3. Breslow, R. Acc. Chem. Res. 1991, 24, 159.

    Article  CAS  Google Scholar 

  4. Dömling, A. Comb. Chem. High Throughput Screening 1998, 1, 1.

    Google Scholar 

  5. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.

    Article  Google Scholar 

  6. Weber, L. Drug Discovery Today 2002, 7, 143.

    Article  CAS  Google Scholar 

  7. Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005.

  8. Wipf, P.; Kendall, C. Chem.–Eur. J. 2002, 8, 1779.

    Google Scholar 

  9. Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.

  10. Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.–Eur. J. 2003, 9, 4286.

    Article  Google Scholar 

  11. (a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 115. (b) Heck, S.; Dömling, A. Synlett 2000, 424.

  12. Weber, L. Curr. Med. Chem. 2002, 9, 2085.

    Article  CAS  Google Scholar 

  13. Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; Wiley: New York, 1983, p. 25.

  14. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.

    Article  CAS  Google Scholar 

  15. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104.

    Article  CAS  Google Scholar 

  16. Maria, M.; Santosa, M. Tetrahedron 2014, 70, 9735.

    Article  Google Scholar 

  17. Pavlovska, T. L.; Redkin, R. Gr.; Lipson, V. V.; Atamanuk, D. V. Mol. Diversity 2016, 20, 299.

    Article  CAS  Google Scholar 

  18. (a) Khalilzadeh, M. A.; Hosseini, A.; Pilevar, A. Eur. J. Org. Chem. 2011, 8, 1587. (b) Salmanpour, S.; Khalilzadeh, M. A.; Hosseini, A. Comb. Chem. High Throughput Screening 2013, 16, 339. (c) Khalilzadeh, M. A.; Keipour, H.; Hosseini, A.; Zareyee, D. New J. Chem. 2014, 38, 42. (d) Hallajian, S.; Khalilzadeh, M. A.; Tajbakhsh, M.; Alipour, E.; Safaei, Z. Comb. Chem. High Throughput Screening 2015, 18, 486.

  19. Sabbaghan, M.; Firooz, A. A.; Ahmadi, V. J. J. Mol. Liq. 2012, 175, 135.

    Article  CAS  Google Scholar 

  20. Habibi, D.; Kaamyabi, S.; Hazarkhani, H. Cuihua Xuebao 2015, 36, 362.

    CAS  Google Scholar 

  21. Babaei, S. E.; Hossaini, Z.; Ramezani Besheli, R.; Tavakkoli, V. Chem. Heterocycl. Compd. 2016, 52, 294. [Khim. Geterotsikl. Soedin. 2016, 52, 294.]

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Gonbad Kavous University, P. O. Box 163, Gonbad, Iran

    Faramarz Rostami-Charati

  2. Department of Chemistry, Qaemshahr Branch, Islamic Azad University, P. O. Box 163, Qaemshahr, Iran

    Zinatossadat Hossaini, Rezvaneh Rostamian, Afshin Zamani & Mahshid Abdoli

  3. Gas Conversion Department, Faculty of Petrochemicals, Iran Polymer and Petrochemical Institute, Tehran, Iran

    Mehdi Ghambarian

Authors
  1. Faramarz Rostami-Charati
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  2. Zinatossadat Hossaini
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  3. Rezvaneh Rostamian
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  4. Mehdi Ghambarian
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  5. Afshin Zamani
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  6. Mahshid Abdoli
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Correspondence to Zinatossadat Hossaini.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(4), 480–483

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Rostami-Charati, F., Hossaini, Z., Rostamian, R. et al. Green synthesis of indol-2-one derivatives from N-alkylisatins in the presence of KF/clinoptilolite nanoparticles. Chem Heterocycl Comp 53, 480–483 (2017). https://doi.org/10.1007/s10593-017-2077-x

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  • DOI: https://doi.org/10.1007/s10593-017-2077-x

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