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Synthesis of spirochromene derivatives catalyzed by Mn(bpyo)2/MCM-41 in water

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Abstract

A three-component one-pot synthesis of spirochromene derivatives by condensing cyclic 1,3-diketones, isatin or acenaphthenequinone, and malononitrile using a catalytic amount of Mn(bpyo)2/MCM-41 in refluxing water is reported.

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References

  1. Bocian W, Kawechi R, Bednarek E, Sitkowski J, Ulkowska A, Kozerski L (2006) New J Chem 30:467

    Article  CAS  Google Scholar 

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

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

    Article  CAS  Google Scholar 

  4. Baird WM, Chang CJ (1990) J Nat Prod 53:23

    Article  Google Scholar 

  5. Pradhan R, Patra M, Behera AK, Mishra BK, Behera RK (2006) Tetrahedron 62:779

    Article  CAS  Google Scholar 

  6. Poupaert J, Carato P, Colacillo E (2005) Curr Med Chem 12:877

    Article  CAS  Google Scholar 

  7. Hiramoto K, Nasuhara A, Michiloshi K, Kato T, Kikugawa K (1997) Mutat Res 395:47

    Article  CAS  Google Scholar 

  8. Joshi KC, Jain R, Arora S (1988) J Indian Chem Soc 65:277

    CAS  Google Scholar 

  9. Joshi KC, Jain R, Arora S (1988) J Indian Chem Soc 65:202

    CAS  Google Scholar 

  10. Elagamay AGA, El-Taweel FMAA (1990) Indian J Chem Sect B29:885

    Google Scholar 

  11. Ballini R, Bosica G, Conforti ML, Maggi R, Mazzacanni A, Righi P, Sartori G (2001) Tetrahedron 57:1395

    Article  CAS  Google Scholar 

  12. Zhu SL, Ji SJ, Zhao K, Zhang Y (2008) Lett Org Chem 5:319

    Article  CAS  Google Scholar 

  13. Dandia A, Jain AK, Bhati DS (2011) Synth Commun 41:2905

    Article  CAS  Google Scholar 

  14. Karimi AR, Sedaghatpour F (2010) Synthesis 10:1731

    Article  Google Scholar 

  15. Dabiri M, Bahramnejad M, Baghbanzadeh M (2009) Tetrahedron 65:9443

    Article  CAS  Google Scholar 

  16. Shanthi G, Subbulakshmi G, Perumal PT (2007) Tetrahedron 63:2057

    Article  CAS  Google Scholar 

  17. Li YL, Chen H, Shi CL, Shi DQ, Ji SJ (2010) J Comb Chem 12:231

    Article  CAS  Google Scholar 

  18. Sridhar R, Srinivas B, Madhav B, Reddy VP, Nageswar YVD, Rao KR (2009) Can J Chem 87:1704

    Article  CAS  Google Scholar 

  19. Wang LM, Jiao N, Qiu J, Yu JJ, Liu JQ, Guo FL, Liu Y (2010) Tetrahedron 66:339

    Article  CAS  Google Scholar 

  20. Heravi MM, Zadsirjan V, Bakhtiari Kh, Oskooie HA, Bamoharram FF (2007) Catal Commun 8:315

    Article  CAS  Google Scholar 

  21. Komiyama T, Takaguchi Y, Tsuboi S (2004) Tetrahedron Lett 45:6299

    Article  CAS  Google Scholar 

  22. Evans DA, Tedrow JS, Shaw JT, Downey W (2002) J Am Chem Soc 124:392

    Article  CAS  Google Scholar 

  23. Sen SE, Smith SM, Sullivan KA (1999) Tetrahedron 55:12657

    Article  CAS  Google Scholar 

  24. Jorgensen KA (1989) Chem Rev 89:431

    Article  Google Scholar 

  25. Zhang W, Jacobsen EN (1991) J Org Chem 56:2296

    Article  CAS  Google Scholar 

  26. Minutolo F, Pini D, Salvadori P (1996) Tetrahedron Lett 37:3375

    Article  CAS  Google Scholar 

  27. Farzaneh F, Soleimannejad J, Ghandi M (1997) J Mol Catal A 118:223

    Article  CAS  Google Scholar 

  28. Luan Z, Xu J, Kevan L (1998) Chem Mater 10:3699

    Article  CAS  Google Scholar 

  29. Caps V, Tsang SC (2000) Catal Today 61:19

    Article  CAS  Google Scholar 

  30. Zhao D, Goldfarb D (1995) J Chem Soc Chem Commun 875

  31. Zhang W, Wang J, Tanev PT, Pinnovaia T (1996) J Chem Commun 979

  32. Vetrivel S, Pandurangan A (2004) Appl Catal A 264:243

    Article  CAS  Google Scholar 

  33. Armbruster U, Martin A, Smejkal Q, Kosslick H (2004) Appl Catal A 265:237

    Article  CAS  Google Scholar 

  34. Malakooti R, Farzaneh F, Ghandi M (2006) J Sci Islam Repub Iran 17:43

    CAS  Google Scholar 

  35. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) Catal Commun 8:289

    Article  CAS  Google Scholar 

  36. Heravi MM, Derikvand F, Ranjbar L, Oskooie HA, Bamoharram FF (2007) J Mol Catal A Chem 261:156

    Article  CAS  Google Scholar 

  37. Heravi MM, Derikvand F, Bamoharram FF (2007) J Mol Catal A Chem 263:112

    Article  CAS  Google Scholar 

  38. Heravi MM, Behbahani FK, Daraie M, Oskooie HA (2009) Mol Divers 13:375

    Article  CAS  Google Scholar 

  39. Heravi MM, Zakeri M, Moharami A (2012) J Chem Sci 124:865

    Article  CAS  Google Scholar 

  40. Mobinikhaledi A, Foroughifar N, BodaghiFard MA (2011) Synth Commun 41:441

    Article  CAS  Google Scholar 

  41. Zou Y, Hu Y, Liu H, Shi D (2012) ACS Comb Sci 14:38

    Article  CAS  Google Scholar 

  42. Saeedi M, Heravi MM, Beheshtiha YS, Oskooie HA (2010) Tetrahedron 66:534

    Article  Google Scholar 

  43. Elinsona MN, Ilovaisky AI, Merkulova VM, Belyakov PA, Barba F, Batanero B (2012) Tetrahedron 68:5833

    Article  Google Scholar 

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Acknowledgments

S. Y. Sh. Beheshtiha, is thankful from Alzahra Research Council for the partial financial support taken from his approved grant.

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Mansoureh Daraie, Yahya S. Beheshtiha & Majid M. Heravi

Authors
  1. Mansoureh Daraie
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  2. Yahya S. Beheshtiha
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  3. Majid M. Heravi
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Corresponding author

Correspondence to Majid M. Heravi.

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Daraie, M., Beheshtiha, Y.S. & Heravi, M.M. Synthesis of spirochromene derivatives catalyzed by Mn(bpyo)2/MCM-41 in water. Monatsh Chem 146, 191–198 (2015). https://doi.org/10.1007/s00706-014-1292-8

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  • DOI: https://doi.org/10.1007/s00706-014-1292-8

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