Skip to main content
SpringerLink
Log in

Mn(pbdo)2Cl2/MCM-41 as a green catalyst in multi-component syntheses of some heterocycles

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Mn(pbdo)2Cl2/MCM-41 as a solid acid catalyst was used as an efficient, green, reusable catalyst for an improved and rapid one-pot multi-component reaction in the synthesis of bis-(4-hydroxycoumarin), bis(indolyl)methane, and 4H-benzo[b]pyran derivatives.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  2. L.A. Thomson, J.A. Ellman, Chem. Rev. 96, 555 (1996)

    Article  Google Scholar 

  3. S. Brauch, S.S.V. Berkel, B. Westermann, Chem. Soc. Rev. 42, 4948 (2013)

    Article  CAS  Google Scholar 

  4. D.G. Rivera, F. Leon, O. Concepcion et al., Chem. Eur. J. 19, 6417 (2013)

    Article  CAS  Google Scholar 

  5. S.S.V. Berkel, B.G.M. Bögels, M.A. Wijdeven, et al., Eur. J. Org. Chem. 2012, 3543 (2012)

  6. B.H. Rotstein, S. Zaretsky, V. Rai et al., Chem. Rev. 114, 8323 (2014)

    Article  CAS  Google Scholar 

  7. V. Estevez, M. Villacampa, J. Carlos, Chem. Rev. 43, 4633 (2014)

    Article  CAS  Google Scholar 

  8. A. Domling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    Article  CAS  Google Scholar 

  9. Z. Guo, B. Liu, Q. Zhang, W. Deng, Y. Wang, Chem. Rev. 43, 3480 (2014)

    Article  CAS  Google Scholar 

  10. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature 359, 710 (1992)

    Article  CAS  Google Scholar 

  11. J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCulle, J.B. Higgins, J.L.J. Schlender, Am. Chem. Soc. 114, 10834 (1992)

    Article  CAS  Google Scholar 

  12. P.L. Llewellyn, Y. Ciesla, H. Decher, R. Stadler, F. Schuth, K.K. Unger, Stud. Surf. Sci. Catal. 84, 2013 (1994)

    Article  CAS  Google Scholar 

  13. J. Aguado, D.P. Serrano, M.D. Romero, J.M. Escola, Chem. Commun. 1, 725 (1996)

  14. A. Corma, M. Iglesias, F. Sanchez, Catal. Lett. 39, 153 (1996)

    Article  CAS  Google Scholar 

  15. P.T. Tanev, M. Chibwe, T.J. Pinnavaia, Nature 368, 321 (1994)

    Article  CAS  Google Scholar 

  16. A. Corma, Chem. Rev. 97, 2373 (1997)

    Article  CAS  Google Scholar 

  17. J.M. Thomas, Angew. Chem. Int. Ed. Engl. 38, 3588 (1999)

    Article  Google Scholar 

  18. M. Selvaraj, P.K. Sinha, A. Pandurangan, Microporous. Mesoporous Mater. 70, 81 (2004)

    Article  CAS  Google Scholar 

  19. M. Selvaraj, P.K. Sinha, K.S. Seshadri, A. Pandurangan, Appl. Catal. A. Gen. 265, 75 (2004)

    Article  CAS  Google Scholar 

  20. S. Velu, L. Wang, M. Okazaki, K. Suzuki, T. Tomura, Microporous Mesoporous Mater. 54, 113 (2002)

    Article  CAS  Google Scholar 

  21. I. Sobczak, M. Ziolek, M. Renn, P. Decyk, I. Nowak, M. Daturi, J.-C. Lavalley. Microporous Mesoporous Mater. 74, 23 (2004)

    Article  CAS  Google Scholar 

  22. Q. Zhang, Y. Wang, S. Itsuki, T. Shishido, K. Takehira, J. Mol. Catal. A Chem. 188, 189 (2002)

    Article  CAS  Google Scholar 

  23. S. Vetrivel, A. Pandurangan, J. Mol. Catal. A Chem. 246, 223 (2006)

    Article  CAS  Google Scholar 

  24. T. Katsuki, J. Mol. Catal. A Chem. 113, 87 (1996)

    Article  CAS  Google Scholar 

  25. V. Caps, S.C. Tsang, Catal. Today 61, 19 (2000)

    Article  CAS  Google Scholar 

  26. R. Burch, N. Cruise, D. Gleeson, S.C.J. Tsang, Chem. Soc. Chem. Commun. 951 (1996)

  27. M. Yonemitsu, Y. Tanaka, M. Iwamoto, Chem. Mater. 9, 2679 (1997)

    Article  CAS  Google Scholar 

  28. M.M. Heravi, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, Catal. Commun. 8, 1991 (2007)

    Article  CAS  Google Scholar 

  29. M.M. Heravi, S. Sadjadi, H.A. Oskoole, F.F. Bamoharram, Catal. Commun. 9, 470 (2008)

    Article  CAS  Google Scholar 

  30. M.M. Heravi, F.K. Behbahani, M. Daraie, H.A. Oskooie, Mol. Divers. 13, 375 (2009)

    Article  CAS  Google Scholar 

  31. M.M. Heravi, M. Tajbakhsh, A.N. Ahmadi, B. Mohajerani, Mon. Chem. 137, 175 (2006)

    Article  CAS  Google Scholar 

  32. M.M. Heravi, M. Khorasani, F. Derikvand, F.F. Bamoharram, Catal. Commun. 8, 1886 (2007)

    Article  CAS  Google Scholar 

  33. M.M. Heravi, M. Daraie, F.K. Behbahani, R. Malakooti, Synth. Commun. 40, 1180 (2010)

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  35. M.M. Heravi, Z. Faghihi, JICS 11, 209 (2014)

    Article  CAS  Google Scholar 

  36. M.M. Heravi, S. Moghimi, JICS 8, 306 (2011)

    Article  CAS  Google Scholar 

  37. M.M. Heravi, M. Daraie, Mon. Chem. 145, 1479 (2014)

    Article  CAS  Google Scholar 

  38. M.M. Heravi, S. Moghimi, Tetrahedron Lett. 53, 392 (2012)

    Article  CAS  Google Scholar 

  39. M.M. Heravi, E. Hashemi, Y.S. Beheshtiha et al., J. Mol. Catal. A Chem. 392, 173 (2014)

    Article  CAS  Google Scholar 

  40. M.M. Heravi, F. Mousavizadeh, N. Ghobadi et al., Tetrahedron Lett. 55, 1226 (2014)

    Article  CAS  Google Scholar 

  41. J.W. Hinman, H. Hoeksema, E.L. Caron, W.G. Jackson, J. Am. Chem. Soc. 78, 1072 (1956)

    Article  CAS  Google Scholar 

  42. Y.L. Chen, T.C. Wang, C.C. Tzeng, N.C. Chang, Helv. Chim. Acta 82, 191 (1999)

    Article  CAS  Google Scholar 

  43. R. Nagashima, R. O’Reilly, G. Levy, Clin. Pharm. Ther. 1, 22 (1969)

    Article  Google Scholar 

  44. C. Stacchino, R. Spano, A. Pettiti, Bull. Chim. Farm. 122, 158 (1983)

    CAS  Google Scholar 

  45. J.S. McIntyre, A.R. Knight, US 3 511 856 (Cl 260-343.2, C07d, A01n), 12 May 1970, Appl. 24 Jun 1968; 3 pp

  46. I. Manolov, C. Maichle-Moessmer, N. Danchev, Eur. J. Med. Chem. 41, 882 (2006)

    Article  CAS  Google Scholar 

  47. M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A Chem. 268, 76 (2007)

    Article  CAS  Google Scholar 

  48. M. Chakrabarty, R. Basak, N. Harigaya, Ghosh. Tetrahedron Lett. 43, 4075 (2002)

    Article  CAS  Google Scholar 

  49. G. Bifulco, I. Bruno, R. Riccio, J. Lavayre, G. Bourdy, J. Nat. Prod. 58, 1254 (1995)

    Article  CAS  Google Scholar 

  50. T.R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa, H. Yukawa, J. Nat. Prod. 63, 596 (2000)

    Article  CAS  Google Scholar 

  51. R.J. Sundberg, The Chemistry of Indoles (Academic Press, New York, 1996)

    Google Scholar 

  52. R. Bell, S. Carmeli, N. Sar, J. Nat. Prod. 57, 1587 (1994)

    Article  CAS  Google Scholar 

  53. E. Fahy, B.C.M. Porn, D.J. Faulkner, K. Smith, J. Nat. Prod. 54, 564 (1991)

    Article  CAS  Google Scholar 

  54. X. Ge, S. Yannai, G. Rennert, N. Gruener, F.A. Fares, Biochem. Biophys. Res. Commun. 228, 153 (1996)

    Article  CAS  Google Scholar 

  55. G. Penieres Carrillo, J.G. Garcia Estrada, J.L. Gutierrez Ramirez, C. Alvarez Tolendano, Green Chem. 5, 337 (2003)

    Article  CAS  Google Scholar 

  56. A.V. Reddy, Y. Venkateseswarlu, Synth. Commun. 33, 3687 (2003)

    Article  Google Scholar 

  57. A. Kamal, A.A. Qureshi, Tetrahedron 19, 513 (1963)

    Article  CAS  Google Scholar 

  58. J.S. Yadav, B.V.S. Reddy, C.V.S.R. Murthy, G.M. Kumar, C. Madan, Synthesis 5, 783 (2001)

  59. G.R. Green, J.M. Evans, A.K. Vong, in Comprehensive Heterocyclic Chemistry II, ed. by A.R. Katritzky, C.W. Rees, E.F.V Scriven, vol. 5 (Pergamon Press, Oxford, 1995), p. 469

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

    Article  CAS  Google Scholar 

  61. S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. 1202 (1988)

  62. L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Lio, J. Fluor. Chem. 127, 97 (2006)

    Article  CAS  Google Scholar 

  63. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  64. X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, Synth. Commun. 33, 119 (2003)

    Article  CAS  Google Scholar 

  65. E. Sheikhhosseini, D. Ghazanfari, Iran. J. Catal. 3, 197 (2013)

    Google Scholar 

  66. H.R. Tavakoli, H. Zamani, M.H. Ghorbani, H.E. Habibabadi, Iran. J. Org. Chem. 2, 118 (2009)

    Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge partial financial support from the Alzahra University Research Council.

Author information

Authors and Affiliations

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

    Majid M. Heravi & Mansoureh Daraie

Authors
  1. Majid M. Heravi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mansoureh Daraie
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Majid M. Heravi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Heravi, M.M., Daraie, M. Mn(pbdo)2Cl2/MCM-41 as a green catalyst in multi-component syntheses of some heterocycles. Res Chem Intermed 42, 2979–2988 (2016). https://doi.org/10.1007/s11164-015-2191-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2191-2

Keywords

Search

Navigation