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Lewis acidic mesoporous Fe-TUD-1 as catalysts for synthesis of Hantzsch 1,4-dihydropyridine derivatives

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Abstract

Lewis acidic mesoporous material (TUD-1) containing Fe was investigated as stable and reusable catalyst for the synthesis of Hantzsch 1,4-dihydropyridine (DHP) derivatives. Yields between 76 and 91 % of DHP derivatives were obtained in shorter reaction times of 3 h depending on the nature of substituents in benzaldehyde.

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References

  1. A. Corma, H. García, Chem. Rev. 103, 4307 (2003)

    Article  CAS  Google Scholar 

  2. K. Wilson, J.H. Clark, Pure Appl. Chem. 72, 1313 (2000)

    Article  CAS  Google Scholar 

  3. M. Jose Climent, A. Corma, S. Iborra, RSC Adv 2, 16 (2012)

    Article  Google Scholar 

  4. S.D. Sawant, M. Srinivas, G. Lakshma Reddy, V. Venkateswar Rao, P.P. Singh, R.A. Vishwakarma, Tetrahedron Lett. 53, 6195 (2012)

    Article  CAS  Google Scholar 

  5. M. Syamala, Org. Prep. Proced. Int. 41, 1 (2009)

    Article  CAS  Google Scholar 

  6. Z.-G. Cheng, X.-Y. Dai, L.-W. Li, Q. Wan, X. Ma, G.-Y. Xiang, Molecules 19, 1344 (2014)

    Article  Google Scholar 

  7. M. Filipan-Litvić, M. Litvić, I. Cepanec, V. Vinković, Molecules 12, 2546 (2007)

    Article  Google Scholar 

  8. S. Wirtz, S. Herzig, Br. J. Pharmacol. 142, 275 (2004)

    Article  CAS  Google Scholar 

  9. J.-P. Wan, Y. Liu, RSC Adv. 2, 9763 (2012)

    Article  CAS  Google Scholar 

  10. Suresh, D. Kumar, J.S. Sandhu, Synth. Commun. 39, 1957 (2009)

    Article  CAS  Google Scholar 

  11. K.L. Bridgwood, G.E. Veitch, S.V. Ley, Org. Lett. 10, 3627 (2008)

    Article  CAS  Google Scholar 

  12. M.M. Heravi, B. Baghernejad, H.A. Oskooie, R. Hekmatshoar, Tetrahedron Lett. 49, 6101 (2008)

    Article  CAS  Google Scholar 

  13. M.M. Heravi, K. Bakhtiari, N.M. Javadi, F.F. Bamoharram, M. Saeedi, H.A. Oskooie, J. Mol. Catal. Chem. 264, 50 (2007)

    Article  CAS  Google Scholar 

  14. H.G.O. Alvim, G.A. Bataglion, L.M. Ramos, A.L. de Oliveira, H.C.B. de Oliveira, M.N. Eberlin, J.L. de Macedo, W.A. da Silva, B.A.D. Neto, Appl. Org. Synth. 70, 3306 (2014)

    CAS  Google Scholar 

  15. N. Isambert, M. del M.S. Duque, J.-C. Plaquevent, Y. Genisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347 (2011)

  16. R. Liu, J. Zhang, Asian J. Chem. 23, 1743 (2011)

    CAS  Google Scholar 

  17. B. Jahanbin, A. Davoodnia, H. Behmadi, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 33, 2140 (2012)

    Article  CAS  Google Scholar 

  18. B.R.P. Kumar, P. Masih, C.R. Lukose, N. Abraham, D. Priya, R.M. Xavier, K. Saji, L. Adhikary, J. Heterocycl. Chem. 46, 336 (2009)

    Article  CAS  Google Scholar 

  19. R. Surasani, D. Kalita, A.V.D. Rao, K. Yarbagi, K.B. Chandrasekhar, J. Fluor. Chem. 135, 91 (2012)

    Article  CAS  Google Scholar 

  20. P.P. Ghosh, P. Mukherjee, A.R. Das, RSC Adv. 3, 8220 (2013)

    Article  CAS  Google Scholar 

  21. R. Pagadala, S. Maddila, V.D.B.C. Dasireddy, S.B. Jonnalagadda, Catal. Commun. 45, 148 (2014)

    Article  CAS  Google Scholar 

  22. A.M. Zonouz, S.B. Hosseini, Synth. Commun. 38, 290 (2008)

    Article  CAS  Google Scholar 

  23. M. Nasr-Esfahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, H. Nasrabadi, J. Mol. Catal. Chem. 382, 99 (2014)

    Article  CAS  Google Scholar 

  24. N. Ahmed, Z.N. Siddiqui, J. Mol. Catal. Chem. 394, 232 (2014)

    Article  CAS  Google Scholar 

  25. A. Heydari, S. Khaksar, M. Tajbakhsh, H.R. Bijanzadeh, J. Fluor. Chem. 130, 609 (2009)

    Article  CAS  Google Scholar 

  26. S. Ghosh, F. Saikh, J. Das, A.K. Pramanik, Tetrahedron Lett. 54, 58 (2013)

    Article  CAS  Google Scholar 

  27. P.P. Ghosh, S. Paul, A.R. Das, Tetrahedron Lett. 54, 138 (2013)

    Article  CAS  Google Scholar 

  28. M.P. Pachamuthu, K. Shanthi, R. Luque, A. Ramanathan, Green Chem. 15, 2158 (2013)

    Article  CAS  Google Scholar 

  29. K. Kandasamy, M.P. Pachamuthu, M. Muthusamy, S. Ganesabaskaran, A. Ramanathan, RSC Adv. 3, 25367 (2013)

    Article  CAS  Google Scholar 

  30. M.P. Pachamuthu, V.V. Srinivasan, R. Maheswari, K. Shanthi, A. Ramanathan, Appl. Catal. Gen. 462–463, 143 (2013)

    Article  Google Scholar 

  31. M.P. Pachamuthu, S. Karthikeyan, G. Sekaran, R. Maheswari, A. Ramanathan, Clean: Soil Air Water 43, 375–381 (2015)

    CAS  Google Scholar 

  32. A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50, 5248 (2009)

    Article  CAS  Google Scholar 

  33. C.A. Antonyraj, S. Kannan, Appl. Catal. Gen. 338, 121 (2008)

    Article  CAS  Google Scholar 

  34. S. Haddoum, I. Fechete, B. Donnio, F. Garin, D. Lutic, C.E. Chitour, Catal. Commun. 27, 141 (2012)

    Article  CAS  Google Scholar 

  35. M. S. Hamdy, G. Mul, J. C. Jansen, A. Ebaid, Z. Shan, A. R. Overweg, and T. Maschmeyer, Catal. Sustain. Future 11th Nord. Symp. Catal. 100, 255 (2005)

  36. M. Akçay, Appl. Catal. Gen. 294, 156 (2005)

    Article  Google Scholar 

  37. D.M. Do, S. Jaenicke, G.-K. Chuah, Catal. Sci. Technol. 2, 1417 (2012)

    Article  CAS  Google Scholar 

  38. N. Koukabi, E. Kolvari, A. Khazaei, M.A. Zolfigol, B. Shirmardi-Shaghasemi, H.R. Khavasi, Chem. Commun. 47, 9230 (2011)

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge the University Grants Commission, New Delhi for financial assistance (F. No. 39-730/2010(SR)). The author would like to thank DST (FIST), UGC (SAP) to procure instrumental facilities in Anna University and IITM-SAIF for NMR analysis.

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Correspondence to Rajamanickam Maheswari.

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Srinivasan, V.V., Pachamuthu, M.P. & Maheswari, R. Lewis acidic mesoporous Fe-TUD-1 as catalysts for synthesis of Hantzsch 1,4-dihydropyridine derivatives. J Porous Mater 22, 1187–1194 (2015). https://doi.org/10.1007/s10934-015-9995-8

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  • DOI: https://doi.org/10.1007/s10934-015-9995-8

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