Enamino ester synthesis using a proton exchanged Algerian montmorillonite clay as acid eco-friendly catalyst
DOI:
https://doi.org/10.22399/ijcesen.4299Keywords:
β-enamino ester, alkyl amines, aromatic amines, β-cetoesters, Maghnite-H+Abstract
An efficient and straightforward methodology has been developed for the synthesis of β-enamino ester derivatives (3a-h). This transformation involves the direct condensation of alkyl or aromatic amines (2a-d) with β-ketoesters (1a-b), facilitated by protonated Algerian montmorillonite clay (MMT-H+) as a heterogeneous, eco-friendly catalyst. The protocol yields the target products in good to excellent yields.The key advantage of this method lies in the utilization of the MMT-H+ catalyst, which is notable for its natural abundance, low cost, and non-toxic nature. As a solid acid, it simplifies the work-up procedure and can be recovered and reused over several cycles without a significant decrease in its catalytic performance. This approach, characterized by its operational simplicity, cost-effectiveness, and environmental friendliness, represents a sustainable alternative for the preparation of these valuable synthetic intermediates.
References
1. Michael, J. P., De Koning, C. B., Gravestock, D., Hosken, G. D., Howard, A. S., Jungmann, C. M., ... & Stanbury, T. V. Pure and applied chemistry. 1999, 71, 979-988.
2. Elliott, M. C.; Wood, J. L.; Wordingham, S. V. Heterocycl Chem. 2005, 10, 73−95.
3. Chattopadhyay, A. K.; Hanessian, S. Chemical Communications. 2015, 51, 16450−16467.
4. Thombal, R. S., & Lee, Y. R. Organic Letters. 2018, 20(15), 4681-4685.
5. Yang, L.; Wei, L.; Wan, J.-P. Chemical Communication. 2018, 54, 7475−7478.
6. Khan, H. P. A.; Chakraborty, T. K. The Journal of Organic Chemistry. 2018, 83, 2027−2039.
7. Greenhill, J. V. Enaminones. Chemical Society Reviews. 1977, 6(3), 277-294.
8. Chaaban, I., Greenhill, J. V., & Akhtar, P. Journal of the Chemical Society, Perkin Transactions 1. 1979, 1593-1596.
9. Michael, J. P., De Koning, C. B., Gravestock, D., Hosken, G. D., Howard, A. S., Jungmann, C. M., ... & Stanbury, T. V. Pure and applied chemistry. 1999, 71, 979-988.
10. Spivey, A. C., Srikaran, R., Diaper, C. M., & Turner, D. J. Organic & biomolecular chemistry. 2003, 1(10), 1638-1640.
11. Souza, F. R., Souza, V. T., Ratzlaff, V., Borges, L. P., Oliveira, M. R., Bonacorso, H. G., ... & Mello, C. F. European journal of pharmacology. 2002, 451(2), 141-147.
12. Hussaini, S. R.; Chamala, R. R.; Wang, Z. Tetrahedron. 2015, 71, 6017-6086.
13. Edafiogho, I. O., Kombian, S. B., Ananthalakshmi, K. V., Salama, N. N., Eddington, N. D., Wilson, T. L., ... & Scott, K. R. Journal of pharmaceutical sciences. 2007, 96(10), 2509-2531.
14. Wang, Y. F., Izawa, T., Kobayashi, S., & Ohno, M. Journal of the American Chemical Society. 1982, 104(23), 6465-6466.
15. Michael, J. P.; De Koning, C. B.; Hosken, G. D.; Stanbury, T. V. Tetrahedron. 2001, 57, 9635–9648.
16. Foster, J. E.; Nicholson, J. M.; Butcher, R.; Stables, J. P.; Edafiogho, I. O.; Goodwin, A. M.; Henson, M. C.; Smith C. A.; Scott, K. R. Bioorg. Med. Chem. 1999, 7, 2415–2425.
17. Boger, D. L.; Ishizaki, T.; Wysocki, R. J. J.; Munk, S. A.; Kitos P. A.; Suntornwat, O. Journal of the American Chemical Society. 1989, 111, 6461–6463.
18. Tietze, L. F.; Vob, E. Tetrahedron Lett.1986, 27, 6181–6184.
19. Martin, R. S.; De Marigorta, E.M. Tetrahedron. 1991, 50, 2255–2264.
20. Figueiredo, L. J. O.; Kascheres, C. The Journal of Organic Chemistry. 1997, 62, 1164–1167.
21. Aumann, R.; Gotlkrr-Schnetmann, I.; Frotlich, R.; Enketo, P. S.; Holst, C. Chemistry–A European Journal. J. 2001, 7, 711–720.
22. Michael, J. P. Pure and applied chemistry. 1997, 69, 583–588.
23. Martin, D. F.; Janusonis, G. A.; Martin, B. B. Journal of the American Chemical Society. 1961, 83, 73–75.
24. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis. 1983, 11, 902–903.
25. Kouadri, Y., Ouahrani, M. R., Missaoui, B. E., Chebrouk, F., & Gherraf, N. Asian Journal of Chemistry. 2015, 27(10), 3676.
26. Bartoli, G.; Bosco, M.; Locatelli, M.; Marcantoni, E.; Melchiorre, P.; Sambri. Synlett. 2004, 239–242.
27.Khosropour, A. R.; Khodaei, M. M.; Kookhazadeh, M. Tetrahedron Lett. 2004, 45, 1725–172
28. Khodaei, M. M.; Khosropour, A. R.; Kookhazadeh, M. Synlett. 2004, 1980–1984.
29. Lenin, R.; Madhusudhan R., R. Arkivoc. 2007, XIII, 204–209.
30. Paira, M.; Misra, R.; Roy, S. C. Indian J. Chem. 2008, 47B, 966–969.
31. Hideo, I.; Yoshifumi, Y.; Chihiro, K. The Journal of Organic Chemistry. 1980, 45, 2938–2942.
32. Murthy, Y. L. N.; Venu, R.; Govindh, B.; Diwakar, B. S.; Naga Lakshmi, K.; Singh, E. R. Asian Journal of Chemistry. 2010, 22, 3047–3053.
33. Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F. Green Chem. 2003, 5, 64–67.
34. Zhang, Z. H.; Hu, J. Y. Journal of the Brazilian Chemical Society. 2006, 17, 1447–1451.
35. Yadav, J. S.; Kumar, V. N.; Rao, R. S.; Priyadarshini, A. D.; Rao, P. P.; Reddy, B. V. S.; Nagaiah, K. Journal of Molecular Catalysis A: Chemical. 2006, 256, 234–237.
36. Masoumeh, M., Farhad, S., Mohadeseh, S., Masoumeh, M. Polycyclic Aromatic Compounds. doi: 10.1080/10406638.2018.1454967.
37. Belbachir, M., Bensaoula, A. (2006). Composi-tion and method for catalysis using bentonites. U. S. Pat., US 7,094,823 B2, 2006.
38. Benlahreche, B., Taleb, Assya., Lahrech, M. B., Hacini, S. Bulletin of Chemical Reaction Engineering & Catalysis. 2019, 14 (3): 551-557
39. Souli, L., Meghabar, R., Djemoui, A., Lahrech, M. B., Belbachir,M. (2015). J. Chem. Pharm. Res. 2015, 7(10):108-115.
40. Ayat, M., Belbachir, M., Rahmouni, A. Bulletin of Chemical Reaction Engineering & Catalysis. 2016, 11(3):376-388.
41. Kherroub, D. E., Belbachir, M., Lamouri, S. Bulletin of Chemical Reaction Engineering & Catalysis. 2014, 9 (1):74-80
42. Belbachir M.; Bensaoula A., Composition and method for using Bentonites. US Patent., 6274,527 B1, 2001.
43. Harrane, A., Meghabar, R., & Belbachir, M. Reactive and Functional Polymers. 2006, 66(12), 1696-1702.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2025 International Journal of Computational and Experimental Science and Engineering

This work is licensed under a Creative Commons Attribution 4.0 International License.