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Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives

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Abstract

Saccharose was applied as a green and natural catalyst for the one-pot, three-component condensation between aromatic aldehydes, malononitrile, and resorcinol, or 4-hydroxycoumarine to afford the corresponding pyran-annulated heterocyclic systems. This green methodology offers several advantages such as the use of a non-hazardous catalyst, easy access, clean work-up, excellent yields, short reaction time, and environmentally mild conditions. In addition, 1,8-dioxodecahydroacridine and 2-substituted benzimidazole derivatives have been synthesized from commercially available starting materials, arylaldehydes, dimedone, amines, or ammonium acetate and o-phenylenediamine using the mentioned catalyst.

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References

  1. F.M. Dean, Naturally occurring oxygen ring compounds (Butterworths, London, 1963)

    Google Scholar 

  2. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    Article  CAS  Google Scholar 

  3. G.M. Cingolani, F. Gualtteri, M. Pigin, J. Med. Chem. 12, 531 (1969)

    Article  CAS  Google Scholar 

  4. J.Y.C. Wu, W.F. Fong, J.X. Zhang, C.H. Leung, H.L. Kwong, M.S. Yang, D. Li, H.Y. Cheung, Eur. J. Pharmacol. 473, 9 (2003)

    Article  CAS  Google Scholar 

  5. P.G. Baraldi, S. Manfredini, D. Simoni, M. Aghazadeh Tabrizi, J. Balzarini, E. De Clercq, J. Med. Chem. 35, 1877 (1992)

    Article  CAS  Google Scholar 

  6. Y. Kashman, K.R. Gustafson, R.W. Fuller, J.H. Cardellina II, J.B. McMahon, M.J. Currens, R.W. Buckheit Jr, S.H. Hughes, G.M. Cragg, M.R. Boyd, J. Med. Chem. 35, 2735 (1992)

    Article  CAS  Google Scholar 

  7. L.L. Andreani, E. Lapi, Boll. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  8. G.P. Ellis, In Chromenes, Chromanones and Chromones; A. Weissberger, Taylor, E. C. Eds.; John Wiley & Sons: New York (1977)

  9. D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seoane, J. Org. Chem. 54, 3069 (1989)

    Article  CAS  Google Scholar 

  10. F.F. Abdel-Latif, Indian J. Chem., Sect B, 29B, 664 (1990)

  11. Y. Peng, G. Song, Catal. Commun. 8, 111 (2007)

    Article  CAS  Google Scholar 

  12. T.S. Jin, L.B. Liu, Y. Zhao, T.S. Li, Synth. Commun. 35, 1859 (2005)

    Article  CAS  Google Scholar 

  13. N. Seshu Babu, N. Pasha, K.T. Venkateswara Rao, P.S. Sai Prasad, N. Lingaiah, Tetrahedron Lett. 49, 2730 (2008)

  14. M.M. Heravi, Y.S. Beheshtiha, Z. Pirnia, S. Sadjadi, M. Adibi, Synth. Commun. 39, 3663 (2009)

    Article  CAS  Google Scholar 

  15. T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Ultrason. Sonochem. 11, 393 (2004)

    CAS  Google Scholar 

  16. N. Martin, C. Seoane, J.L. Soto, Tetrahedron 44, 5861 (1988)

    Article  CAS  Google Scholar 

  17. V.D. Dyachenko, Russ. J. Gen. Chem. 76, 282 (2006)

    Article  CAS  Google Scholar 

  18. K. Gong, H.L. Wang, J. Luo, Z.L. Liu, J. Heterocycl. Chem. 46, 1145 (2009)

    Article  CAS  Google Scholar 

  19. S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64, 9143 (2008)

    Article  CAS  Google Scholar 

  20. S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  21. D.S. Raghuvanshi, K.N. Singh, Arkivoc x, 305 (2010)

  22. S. Makarem, A.A. Mohammadi, A.R. Fakhari, Tetrahedron Lett. 49, 7194 (2008)

    Article  CAS  Google Scholar 

  23. S.A. Gamaga, J.A. Spicer, G.J. Atwell, G.J. Finlay, B.C. Baguley, W.A. Denny, J. Med. Chem. 42, 2383 (1999)

    Article  Google Scholar 

  24. I. Antonini, P. Polucci, L.R. Kelland, E. Menta, N. Pescalli, S. Martelli, J. Med. Chem. 42, 2535 (1999)

    Article  CAS  Google Scholar 

  25. Y. Mikata, M. Yokoyama, K. Mogami, M. Kato, I. Okura, M. Chikira, S. Yano, Inorganica Chim. Acta 279, 51 (1998)

    Article  CAS  Google Scholar 

  26. S. Gallo, S. Atifi, A. Mohamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, J. Barbe, Eur. J. Med. Chem. 38, 19 (2003)

    Article  CAS  Google Scholar 

  27. L. Ngadi, A.M. Galy, J.P. Galy, J. Barbe, A. Crémieux, J. Chevalier, D. Sharples, Eur. J. Med. Chem. 25, 67 (1990)

    Article  CAS  Google Scholar 

  28. M. Wainwright, J. Antimicrob. Chemother. 47, 1 (2001)

    Article  CAS  Google Scholar 

  29. M. Kidwai, D. Bhatnagar, Tetrahedron Lett. 51, 2700 (2010)

    Article  CAS  Google Scholar 

  30. W. Shen, L.M. Wang, H. Tian, J. Tang, J.J. Yu, J. Fluor Chem. 130, 522 (2009)

    Article  CAS  Google Scholar 

  31. D.Q. Shi, S.N. Ni, F. Yang, J.W. Shi, G.L. Dou, X.-Y. Li, X.-S. Wang, J. Heterocycl Chem. 45, 653 (2008)

    Article  CAS  Google Scholar 

  32. M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun. 9, 939 (2008)

    Article  CAS  Google Scholar 

  33. K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun. 39, 228 (2009)

    Article  CAS  Google Scholar 

  34. B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A Chem. 247, 233 (2006)

    Article  CAS  Google Scholar 

  35. A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)

    Article  CAS  Google Scholar 

  36. F. Rashedian, D. Saberib, K. Niknam, J. Chin. Chem. Soc. 57, 998 (2010)

    Article  CAS  Google Scholar 

  37. T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synthesis 12, 2001 (2004)

    Article  Google Scholar 

  38. G. Mohammadi Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. J. Chem. 2011, doi:10.1016/j.arabjc.2011.01.037

  39. N. Hazeri, A. Masoumnia, M.T. Mghsoodlou, S. Salahi, M. Kangani, S. Kianpour, S. Kiaee, J. Abonajmi. Res. Chem. Intermed. doi:10.1007/s11164-013-1516-2

  40. W.A. Denny, G.W. Rewcastle, B.C. Baguley, J. Med. Chem. 33, 814 (1990)

    Article  CAS  Google Scholar 

  41. T. Fonseca, B. Gigante, T.L. Gilchrist, Tetrahedron 57, 1793 (2001)

    Article  CAS  Google Scholar 

  42. Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada, T. Naka, J. Med. Chem. 39, 5228 (1996)

    Article  CAS  Google Scholar 

  43. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, L.B. Townsend, J. Med. Chem. 41, 1252 (1998)

    Article  CAS  Google Scholar 

  44. H. Zarrinmayeh, D.M. Zimmerman, B.E. Cantrell, D.A. Schober, R.F. Bruns, S.L. Gackenheimer, P.L. Ornstein, P.A. Hipskind, T.C. Britton, D.R. Gehlert, Bioorg. Med. Chem. Lett. 9, 647 (1999)

    Article  CAS  Google Scholar 

  45. N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 391 (2014)

    Article  CAS  Google Scholar 

  46. N. Hazeri, M.T. Maghsoodlou, M.R. Mousavi, J. Aboonajmi, M. Safarzaei, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1179-z

    Google Scholar 

  47. M.R. Mousavi, N. Hazeri, M.T. Maghsoodlou, S. Salahi, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 411 (2013)

    Article  CAS  Google Scholar 

  48. N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, M. Norouzi, M. Moin, S. Mohamadian-Souri, J. Chem. Res. 550 (2013)

  49. M. Kidwai, S. Saxena, Synth. Commun. 36, 2737 (2006)

    Article  CAS  Google Scholar 

  50. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  51. D.-Q. Shi, J. Wang, Q.-Y. Zhuang, X.-S. Wang, Chin. J. Org. Chem. 26, 643 (2006)

    CAS  Google Scholar 

  52. M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)

    Article  CAS  Google Scholar 

  53. R.M. Shaker, Pharmazie 51, 148 (1996)

    CAS  Google Scholar 

  54. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  55. H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)

    Article  CAS  Google Scholar 

  56. F.K. Behbahani, P. Ziaei, Chem. Heterocycl. Compd. 48, 1011 (2012)

    Article  CAS  Google Scholar 

  57. H.M. Bachhav, S.B. Bhagat, V.N. Telvekar, Tetrahedron Lett. 52, 5697 (2011)

    Article  CAS  Google Scholar 

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Correspondence to Malek Taher Maghsoodlou.

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Maghsoodlou, M.T., Hazeri, N., Lashkari, M. et al. Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives. Res Chem Intermed 41, 6985–6997 (2015). https://doi.org/10.1007/s11164-014-1793-4

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