Skip to main content
Log in

Solvent free, environment benign synthesis of 1,4-dihydropyridines and polyhydroquinolines by using heterogeneous Zn/MCM-41 catalyst

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

Abstract

Heterogeneous catalysis has been utilized in number of efficient reactions with higher selectivity of the product, more stable, reusable and easy for separation as compared to homogeneous catalysts. Generally, heterogeneous catalysts are prepared by using mesoporous materials, microporous materials, metal oxides and metal organic framework. The mesoporous materials have small particle size and high surface area as compared to the microporous materials. The adsorbent mesoporous materials have highly efficient for the therapeutic applications in chemistry hence it has best as compared to other heterogeneous materials. Herein, we have reported synthesis of 1,4-dihydropyridines and polyhydroquinolines at solvent free and environmental benign condition in the presence of Zn/MCM-41 catalyst. The present protocol gives excellent yield (89–96%) of the product within short reaction time by easy work up procedure and no need of further purification of product. The catalyst was characterized by XRD diffractometer, SEM, EDAX, TGA-DTA, BET surface area analysis and FT-IR Spectroscopy. The synthesized organic compounds were characterized by FT-IR, 1H NMR, 13C NMR, LC–MS spectrometry.

Graphical abstract

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Y. F. Xu, P. N. Duchesne, L. Wang, A. Tavasoli, A. A. Jelle, M. Xia, J. F. Liao, D. Bin Kuang, and G. A. Ozin, Nat. Commun. 11, (2020)

  2. J. Zdarta, A. S. Meyer, T. Jesionowski, and M. Pinelo, Catalysts 8, (2018)

  3. S.S. Chen, D.C.W. Tsang, J.P. Tessonnier, Appl. Catal. B Environ. 261, 118126 (2020)

    Article  CAS  Google Scholar 

  4. S. Liu, Y.J. Lei, Z.J. Xin, Y. Bin Lu, H.Y. Wang, J. Photochem. Photobiol. A Chem. 355, 141 (2018)

    Article  CAS  Google Scholar 

  5. B. Subotić, T. Antonić Jelić, J. Bronić, Stud. Surf. Sci. Catal. 170, 233 (2007)

    Article  Google Scholar 

  6. M.E. Davis, Nature 417, 813 (2002)

    Article  CAS  PubMed  Google Scholar 

  7. C. Laurino, B. Palmieri, Nutr. Hosp. 32, 573 (2015)

    CAS  PubMed  Google Scholar 

  8. T. Asefa, V. Dubovoy, Comprehens. Supramol. Chem. 2, 157 (2017)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  10. F. Catalano, P. P. Pompa, A. Barrabino, Y. He, J. J. Li, M. Long, S. Liang, H. Xu, E. D. M. Isa, H. Ahmad, M. B. A. Rahman, M. Kruk, M. Jaroniec, H. J. Shin, R. Ryoo, V. der AA, Y. Chiang, H. Lian, S. Leo, S. Wang, Y. Yamauchi, K. C. Wu, W. He, Y. Yang, J. J. Li, L. Long, K. Zhang, Y. Xiang, S. Qin, J. Yu, M. E. Habibollah, Y. Afsaneh, Y. Castro, N. I. Vazquez, and Z. Gonzalez, Alg. Dagbl. 457, 47237 (2017).

  11. A. Corma, Chem. Rev. 95, 559 (1995)

    Article  CAS  Google Scholar 

  12. 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. McCullen, J.B. Higgins, J.L. Schlenker, J. Am. Chem. Soc. 114, 10834 (1992)

    Article  CAS  Google Scholar 

  13. L.B. McCusker, F. Liebau, G. Englehardt, Microporous Mesoporous Mater. 58, 3 (2003)

    Article  CAS  Google Scholar 

  14. G.D. Stucky, A. Monnier, F. Schiith, Q. Huo, D. Margolese, D. Kumar, M. Krishnamurty, P. Petroff, A. Firouzi, M. Janicke, B.F. Chmelka, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A. Mol. Cryst. Liq. Cryst. 240, 187 (1994)

    Article  CAS  Google Scholar 

  15. F. Habeche, M. Hachemaoui, A. Mokhtar, K. Chikh, F. Benali, A. Mekki, F. Zaoui, Z. Cherifi, B. Boukoussa, J. Inorg. Organomet. Polym. Mater. 30, 4245 (2020)

    Article  CAS  Google Scholar 

  16. G. Martínez-Edo, A. Balmori, I. Pontón, A. M. Del Rio, and D. Sánchez-García, Catalysts 8 (2018).

  17. A. Ghorbani-Choghamarani, M. Mohammadi, T. Tamoradi, M. Ghadermazi, Polyhedron 158, 25 (2019)

    Article  CAS  Google Scholar 

  18. G. Mohammadi Ziarani, S. Roshankar, F. Mohajer, A. Badiei, Curr. Org. Chem. 25, 361 (2021)

  19. D. Esquivel, E.D. Canck, C. Jimenez-Sanchidrian, P.V.D. Voort, F.J. Romero-Salguero, Curr. Org. Chem. 18, 1280 (2014)

    Article  CAS  Google Scholar 

  20. M. Mohammadi, M. Khodamorady, B. Tahmasbi, K. Bahrami, A. Ghorbani-Choghamarani, J. Ind. Eng. Chem. 97, 1 (2021)

    Article  CAS  Google Scholar 

  21. T. Hama, S. Ge, J.F. Hartwig, J. Org. Chem. 78, 8250 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. P.T. Anastas, M.M. Kirchhoff, Acc. Chem. Res. 35, 686 (2002)

    Article  CAS  PubMed  Google Scholar 

  23. P.T. Anastas, Chemsuschem 2, 391 (2009)

    Article  CAS  PubMed  Google Scholar 

  24. M. Beller, C. Bolm, Transit. Met. Org. Synth. 1, 3 (2004)

    Google Scholar 

  25. X.F. Wu, Chem.—An Asian J. 7, 2502 (2012)

    Article  CAS  Google Scholar 

  26. X.F. Wu, H. Neumann, Adv. Synth. Catal. 354, 3141 (2012)

    Article  CAS  Google Scholar 

  27. J. Silvestre-Albero, J.C. Serrano-Ruiz, A. Sepúlveda-Escribano, F. Rodríguez-Reinoso, Appl. Catal. A Gen. 351, 16 (2008)

    Article  CAS  Google Scholar 

  28. M. Abedini, F. Shirini, M. Mousapour, Res. Chem. Intermed. 42, 2303 (2016)

    Article  CAS  Google Scholar 

  29. H. Ahankar, A. Ramazani, S.W. Joo, Res. Chem. Intermed. 42, 2487 (2016)

    Article  CAS  Google Scholar 

  30. D. Paprocki, A. Madej, D. Koszelewski, A. Brodzka, R. Ostaszewski, Front. Chem. 6, 1 (2018)

    Article  CAS  Google Scholar 

  31. A.A. Patravale, A.H. Gore, D.R. Patil, G.B. Kolekar, M.B. Deshmukh, P.B. Choudhari, M.S. Bhatia, P.V. Anbhule, Res. Chem. Intermed. 42, 2919 (2016)

    Article  CAS  Google Scholar 

  32. G. Sipos, V. Gyollai, T. Sipocz, G. Dormán, L. Kocsis, R.V. Jones, F. Darvas, J. Flow Chem. 3, 51 (2013)

    Article  Google Scholar 

  33. I. Yamanaka, Res. Chem. Intermed. 32, 373 (2006)

    Article  CAS  Google Scholar 

  34. J.N. Sheagren, N. Engl, J. Med. 310, 1368 (1984)

    CAS  Google Scholar 

  35. R. Sridhar, P.T. Perumal, Tetrahedron 61, 2465 (2005)

    Article  CAS  Google Scholar 

  36. P. Mayurachayakul, W. Pluempanupat, C. Srisuwannaket, O. Chantarasriwong, RSC Adv. 7, 56764 (2017)

    Article  CAS  Google Scholar 

  37. M. Kazemi, M. Mohammadi, Appl. Organomet. Chem. 34, 42 (2020)

    Article  CAS  Google Scholar 

  38. M.A. Zolfigol, M. Yarie, RSC Adv. 5, 103617 (2015)

    Article  CAS  Google Scholar 

  39. T. Tamoradi, S.M. Mousavi, M. Mohammadi, New J. Chem. 44, 3012 (2020)

    Article  CAS  Google Scholar 

  40. T. Tamoradi, S.M. Mousavi, M. Mohammadi, New J. Chem. 44, 8289 (2020)

    Article  CAS  Google Scholar 

  41. M.A. Zolfigol, H. Ghaderi, S. Baghery, L. Mohammadi, J. Iran. Chem. Soc. 14, 121 (2017)

    Article  CAS  Google Scholar 

  42. M. Maheswara, V. Siddaiah, G.L.V. Damu, C.V. Rao, ARKIVOC 2006, 201 (2006)

    Article  Google Scholar 

  43. J. Davarpanah, M. Ghahremani, O. Najafi, J. Mol. Struct. 1177, 525 (2019)

    Article  CAS  Google Scholar 

  44. S. Sheik Mansoor, K. Aswin, K. Logaiya, S.P.N. Sudhan, Arab. J. Chem. 10, S546 (2017)

    Article  CAS  Google Scholar 

  45. K. Mohammadi, F. Shirini, A. Yahyazadeh, Res. Chem. Intermed. 42, 2047 (2016)

    Article  CAS  Google Scholar 

  46. G. Župan, V. Eraković, A. Simonić, J. Križ, J. Varljen, Prog. Neuro-Psychopharmacol. Biol. Psychiatr. 23, 951 (1999)

    Article  Google Scholar 

  47. R. Farsi, M.K. Mohammadi, S.J. Saghanezhad, Res. Chem. Intermed. 47, 1161 (2021)

    Article  CAS  Google Scholar 

  48. J.K. Satyarthi, L. Saikia, D. Srinivas, P. Ratnasamy, Appl. Catal. A Gen. 330, 145 (2007)

    Article  CAS  Google Scholar 

  49. S.E. Kondawar, A.S. Potdar, C.V. Rode, RSC Adv. 5, 16452 (2015)

    Article  CAS  Google Scholar 

  50. S.E. Kondawar, R.B. Mane, A. Vasishta, S.B. More, S.D. Dhengale, C.V. Rode, Appl. Petrochem. Res. 7, 41 (2017)

    Article  CAS  Google Scholar 

  51. J. Klenc, E. Raux, S. Barnes, S. Sullivan, B. Duszynska, A.J. Bojarski, L. Strekowski, J. Heterocycl. Chem. 46, 1259 (2009)

    Article  CAS  Google Scholar 

  52. M.M. Heravi, M. Hosseini, H.A. Oskooie, B. Baghernejad, F. Farzaneh, Chin. J. Chem. 28, 2045 (2010)

    Article  CAS  Google Scholar 

  53. P. Kulkarni, J. Chil. Chem. Soc. 59, 2319 (2014)

    Article  CAS  Google Scholar 

  54. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 1240 (2017)

    Article  CAS  Google Scholar 

  55. A. Maleki, V. Eskandarpour, J. Rahimi, N. Hamidi, Carbohydr. Polym. 208, 251 (2019)

    Article  CAS  PubMed  Google Scholar 

  56. S. Vaysipour, Z. Rafiee, M. Nasr-Esfahani, Polyhedron 176, 114294 (2020)

    Article  CAS  Google Scholar 

  57. K.M.S. Khalil, J. Colloid Interface Sci. 315, 562 (2007)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

Shankar Dhengale acknowledges the Chhatrapati Shahu Maharaj Research, Training and Human Development Institute (SARTHI), Pune, MH, India, for the award of Chief Minister Special Research fellowship and we have gratefully acknowledged the Research Strengthening Scheme, Shivaji University, Kolhapur for providing assistance for research work (SU/C & U. D. Section/86/1384 Date 28 March 2019)

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Prashant V. Anbhule.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 9158 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dhengale, S.D., Naik, V.M., Kolekar, G.B. et al. Solvent free, environment benign synthesis of 1,4-dihydropyridines and polyhydroquinolines by using heterogeneous Zn/MCM-41 catalyst. Res Chem Intermed 47, 3263–3287 (2021). https://doi.org/10.1007/s11164-021-04473-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04473-z

Keywords

Navigation