Synthesis of novel 6-amino-2-(hydroxymethyl)-8-aryl-7-(phenylsulfonyl)pyrano[3,2-b]pyran-4(8H)-one derivatives catalyzed by nano-cellulose-OSO3H

  • Bahareh SadeghiEmail author


A novel series of 6-amino-2-(hydroxymethyl)-8-aryl-7-(phenylsulfonyl)pyrano[3,2-b]pyran-4(8H)-one derivatives was synthesized via an efficient, mild and rapid protocol. Pyran-annulated heterocycles were obtained in improved yields using aromatic aldehydes, 5-hydroxy-2-hydroxymethyl-4H-pyran-4-one and phenylsulfonylacetonitrile in the presence of nano-cellulose-OSO3H as a suitable and efficient catalyst. Nano-cellulose-OSO3H was synthesized by preparing nano-cellulose as a support, followed by treatment with chlorosulfonic acid (ClSO3H). The proposed protocol represents an eco-friendly approach that provides excellent yields, with mild reaction conditions, ease of workup, survival of different functional groups and short reaction times.


Phenylsulfonylacetonitrile Pyran derivatives Kojic acid Green chemistry Nano-cellulose-OSO3



The research Council of the Islamic Azad University of Yazd is gratefully acknowledged for the financial support for this work.

Supplementary material

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  1. 1.
    R.S. Bon, B. van Vliet, N.E. Sprenkels, R.F. Schmitz, F.J.J. Kanter, C.V. Stevens, M. Swart, F.M. Bickelhaupt, M.B. Groen, R.V.A. Orru, J. Org. Chem. 70, 3542 (2005)CrossRefGoogle Scholar
  2. 2.
    R.V.A. Orru, M. de Greef, Synthesis 10, 1471 (2003)CrossRefGoogle Scholar
  3. 3.
    E. Kolvari, N. Koukabi, M.M. Hosseini, M. Vahidian, E. Ghobadi, RSC Adv. 6, 7419 (2016)CrossRefGoogle Scholar
  4. 4.
    S. Sobhani, S. Rezazadeh, J. Iran. Chem. Soc. 8, 198 (2011)CrossRefGoogle Scholar
  5. 5.
    F. Nemati, A. Elhampour, Res. Chem. Intermed. 42, 7611 (2016)CrossRefGoogle Scholar
  6. 6.
    A. Bamoniri, B.F. Mirjalili, S. Saleh, RSC Adv. 8, 6178 (2018)CrossRefGoogle Scholar
  7. 7.
    M.R. Mousavi, M.T. Maghsoodlou, J. Iran. Chem. Soc. 12, 743 (2015)CrossRefGoogle Scholar
  8. 8.
    W.S. Shehab, A.A. Ghoneim, Arab. J. Chem. 9, S966 (2016)CrossRefGoogle Scholar
  9. 9.
    T.K. Chattapadhyay, P.J. Dureja, J. Agric. Food Chem. 54, 2129 (2006)CrossRefGoogle Scholar
  10. 10.
    S. Uzzaman, A. Mashrai, H. Khanam, M. Asif, A. Ali, A. Sherwani, M. Owais, JKSUS 27, 1 (2015)Google Scholar
  11. 11.
    T. Wang, J. Liu, H. Zhong, H. Chen, Z. Lv, Y. Zhang, M. Zhang, D. Geng, C. Niu, Y. Li, K. Li, Bioorg. Med. Chem. Lett. 21, 3381 (2011)CrossRefGoogle Scholar
  12. 12.
    A.D. Patil, A.J. Freyer, D.S. Eggleston, R.C. Haltiwanger, M.F. Bean, P.B. Taylor, M.J. Caranfa, A.L. Breen, H.R. Bartus, J. Med. Chem. 36, 4131 (1993)CrossRefGoogle Scholar
  13. 13.
    M. Jereb, Green Chem. 14, 3047 (2012)CrossRefGoogle Scholar
  14. 14.
    K.M. Elattar, A. Fekri, N.M. Bayoumy, A.A. Fadda, Res. Chem. Intermed. 43, 4227 (2017)CrossRefGoogle Scholar
  15. 15.
    A.A. Fadda, N.M. Bayoumy, K.M. Elattar, Synth. Commun. 45, 2637 (2015)CrossRefGoogle Scholar
  16. 16.
    E.R. El-Sawy, A.H. Mandour, S.M. El-Hallouty, K.H. Shaker, H.M. Abo-Salem, Arab. J. Chem. 6, 67 (2013)CrossRefGoogle Scholar
  17. 17.
    J. Kim, J. Kwon, D. Lee, S. Jo, D.S. Park, J. Choi, E. Park, J.Y. Hwang, Y. Ko, I. Choi, M.K. Ju, Bioorg. Med. Chem. Lett. 23, 153 (2013)CrossRefGoogle Scholar
  18. 18.
    F. Li, Q. Zhu, Y. Zhang, Y. Feng, Y. Leng, A. Zhang, Bioorg. Med. Chem. 18, 3875 (2010)CrossRefGoogle Scholar
  19. 19.
    J.W. Choy, C. Bryant, C.M. Calvet, P.S. Doyle, S.S. Gunatilleke, S.S. Leung, K.K. Ang, S. Chen, J. Gut, J.A. Oses-Prieto, J.B. Johnston, Beilstein. J. Org. Chem. 9, 15 (2013)CrossRefGoogle Scholar
  20. 20.
    A. El-Awa, M.N. Noshi, X.M. du Jourdin, P.L. Fuchs, Chem. Rev. 109, 2315 (2009)CrossRefGoogle Scholar
  21. 21.
    N.R. Haines, A.N. Van Zanten, A.A. Cuneo, J.R. Miller, W.J. Andrews, D.A. Carlson, R.M. Harrington, A.M. Kiefer, J.D. Mason, J.A. Pigza, S.S. Murphree, J. Org. Chem. 76, 8131 (2011)CrossRefGoogle Scholar
  22. 22.
    F. Rajabi, A. Feiz, R. Luque, Catal. Lett. 145, 1621 (2015)CrossRefGoogle Scholar
  23. 23.
    F. Rajabi, F. Fayyaz, R. Luque, Microporous Mesoporous Mater. 253, 64 (2017)CrossRefGoogle Scholar
  24. 24.
    B.F. Mirjalili, A. Bamoniri, M.A. Mirhoseini, Sci. Iran. C 20, 587 (2013)Google Scholar
  25. 25.
    N. Salehi, B.F. Mirjalili, RSC Adv. 7, 30303 (2017)CrossRefGoogle Scholar
  26. 26.
    B.F. Mirjalili, R. Zare Reshquiyea, RSC Adv. 5, 15566 (2015)CrossRefGoogle Scholar
  27. 27.
    B. Sadeghi, Sci. Iran. C 21, 708 (2014)Google Scholar
  28. 28.
    B. Sadeghi, M.H. Sowlat Tafti, J. Iran. Chem. Soc. 13, 1375 (2016)CrossRefGoogle Scholar
  29. 29.
    B. Sadeghi, M. Bouslik, M.R. Shishehbore, J. Iran. Chem. Soc. 12, 1801 (2015)CrossRefGoogle Scholar
  30. 30.
    F. Manouchehri, B. Sadeghi, F. Najafi, M.H. Mosslemin, J. Iran. Chem. Soc. 15, 1673 (2018)CrossRefGoogle Scholar
  31. 31.
    H.R. Molaei, B. Sadeghi, J. Nanostruct. Chem. 8, 197 (2018)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryYazd Branch, Islamic Azad UniversityYazdIran

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