Advertisement

Research on Chemical Intermediates

, Volume 40, Issue 2, pp 699–709 | Cite as

CAN-catalyzed synthesis of 10-arylpyrano[3,2-b]chromene-4,9-diones under solvent-free conditions

  • Yuling Li
  • Xiangxue Meng
  • Gan Cai
  • Baixiang Du
  • Bo Zhao
Article

Abstract

A novel and efficient one-pot synthesis of 10-aryl-7,8-dihydropyrano[3,2-b]chromene-4,9(6H,10H)-diones by three-component reaction of aromatic aldehydes, 5-hydroxy-2-methylpyran-4-one, and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of ceric ammonium nitrate under solvent-free conditions is described. The advantages of this method include operational simplicity, short reaction time, recyclable catalyst, and high yields.

Keywords

MCRs CAN Pyrano[3,2-b]chromene Synthesis Solvent-free 

Notes

Acknowledgments

We are grateful to the National Natural Science Foundation of China (no. 21104064, 21172188), the Natural Science Foundation of Xuzhou Normal University (10XLR03, 11XLR13) and the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

References

  1. 1.
    D.R. da Rocha, A.C.G. de Souza, J.A.L.C. Resende, W.C. Santos, E.A. dos Santos, C. Pessoa, M.O. de Moraes, L.V. Costa-Lotufo, R.C. Montenegro, V.F. Ferreira, Org. Biomol. Chem. 9, 4315 (2011)CrossRefGoogle Scholar
  2. 2.
    S.B. Ferreira, F. de Carvalho da Silva, F.A.F.M. Bezerra, M.C.S. Lourenco, C.R. Kaiser, A.C. Pinto, V.F. Ferreira, Arch. Pharm. 343, 81 (2010)Google Scholar
  3. 3.
    M.Z. He, N. Yang, C.L. Sun, X.J. Yao, M. Yang, Med. Chem. Res. 20, 200 (2010)CrossRefGoogle Scholar
  4. 4.
    A. Shahrisa, M. Zirak, A.R. Mehdipour, R. Miri, Chem. Heterocycl. Compd. 46, 1354 (2011)CrossRefGoogle Scholar
  5. 5.
    R. Schiller, L. Tichotova, J. Pavlik, V. Buchta, B. Melichar, I. Votruba, J. Kunes, M. Spulak, M. Pour, Bioorg. Med. Chem. Lett. 20, 7358 (2010)CrossRefGoogle Scholar
  6. 6.
    H. Hussain, S. Aziz, B. Schulz, K. Krohn, Nat. Prod. Commun. 6, 841 (2011)Google Scholar
  7. 7.
    S. Osman, B.J. Albert, Y.P. Wang, M.S. Li, N.L. Czaicki, K. Koide, Chem. Eur. J. 17, 895 (2011)CrossRefGoogle Scholar
  8. 8.
    S.S. Bisht, N. Jaiswal, A. Sharma, S. Fatima, R. Sharma, N. Rahuja, A.K. Srivastava, V. Bajpai, B. Kumar, R.P. Tripathi, Carbohydr. Res. 346, 1191 (2011)CrossRefGoogle Scholar
  9. 9.
    S.M. Wang, G.W.A. Milne, X.J. Yan, I. Posey, M.C. Nicklaus, L. Graham, W.G. Rice, J. Med. Chem. 39, 2047 (1996)CrossRefGoogle Scholar
  10. 10.
    V.V. Mulwad, V.P. Kewat, Indian J. Heterocycl. Chem. 19, 47 (2009)Google Scholar
  11. 11.
    H. Miyazaki, K. Honda, M. Asami, S. Inoue, J. Org. Chem. 64, 9507 (1999)CrossRefGoogle Scholar
  12. 12.
    J.S. Yadav, B.V.S. Reddy, L. Chandraiah, B. Jagannadh, S.K. Kumar, A.C. Kunwar, Tetrahedron Lett. 43, 4527 (2002)CrossRefGoogle Scholar
  13. 13.
    B.V.S. Reddy, M.R. Reddy, G. Narasimhulu, J.S. Yadav, Tetrahedron Lett. 51, 5677 (2010)CrossRefGoogle Scholar
  14. 14.
    W.L. Li, L.Q. Wu, L. Fu, J. Brazil, Chem. Soc. 22, 2202 (2011)Google Scholar
  15. 15.
    W.L. Li, J.Y. Liang, T.B. Wang, Y.Q. Wang, Collect. Czech. Chem. Commun. 76, 1791 (2011)CrossRefGoogle Scholar
  16. 16.
    M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, P. Machado, Chem. Rev. 109, 4140 (2009)CrossRefGoogle Scholar
  17. 17.
    K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)CrossRefGoogle Scholar
  18. 18.
    V. Sridharan, J.C. Menendez, Chem. Rev. 110, 3805 (2010)CrossRefGoogle Scholar
  19. 19.
    Y.L. Li, B.X. Du, S.X. Wang, D.Q. Shi, S.J. Tu, J. Heterocycl. Chem. 43, 685 (2006)CrossRefGoogle Scholar
  20. 20.
    Y.L. Li, X.P. Xu, D.Q. Shi, S.J. Ji, Chin. J. Chem. 27, 1510 (2009)CrossRefGoogle Scholar
  21. 21.
    Y.L. Li, B.X. Du, X.P. Xu, D.Q. Shi, S.J. Ji, Chin. J. Chem. 27, 1563 (2009)CrossRefGoogle Scholar
  22. 22.
    Crystallographic data for the structures of 4g reported in this paper have been deposited at the Cambridge Crystallographic Data Centre with No. CCDC-891132Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Yuling Li
    • 1
  • Xiangxue Meng
    • 1
  • Gan Cai
    • 1
  • Baixiang Du
    • 1
  • Bo Zhao
    • 1
  1. 1.School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional MaterialsJiangsu Normal UniversityXuzhouChina

Personalised recommendations