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. DOI: https://doi.org/10.1039/C5CC05892A
4. Thombal, R. S., & Lee, Y. R. Organic Letters. 2018, 20(15), 4681-4685. DOI: https://doi.org/10.1021/acs.orglett.8b02008
5. Yang, L.; Wei, L.; Wan, J.-P. Chemical Communication. 2018, 54, 7475−7478. DOI: https://doi.org/10.1039/C8CC03514H
6. Khan, H. P. A.; Chakraborty, T. K. The Journal of Organic Chemistry. 2018, 83, 2027−2039. DOI: https://doi.org/10.1021/acs.joc.7b02962
7. Greenhill, J. V. Enaminones. Chemical Society Reviews. 1977, 6(3), 277-294. DOI: https://doi.org/10.1039/cs9770600277
8. Chaaban, I., Greenhill, J. V., & Akhtar, P. Journal of the Chemical Society, Perkin Transactions 1. 1979, 1593-1596. DOI: https://doi.org/10.1039/p19790001593
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. DOI: https://doi.org/10.1351/pac199971060979
10. Spivey, A. C., Srikaran, R., Diaper, C. M., & Turner, D. J. Organic & biomolecular chemistry. 2003, 1(10), 1638-1640. DOI: https://doi.org/10.1039/B303064D
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. DOI: https://doi.org/10.1016/S0014-2999(02)02225-2
12. Hussaini, S. R.; Chamala, R. R.; Wang, Z. Tetrahedron. 2015, 71, 6017-6086. DOI: https://doi.org/10.1016/j.tet.2015.06.026
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. DOI: https://doi.org/10.1002/jps.20967
14. Wang, Y. F., Izawa, T., Kobayashi, S., & Ohno, M. Journal of the American Chemical Society. 1982, 104(23), 6465-6466. DOI: https://doi.org/10.1021/ja00387a060
15. Michael, J. P.; De Koning, C. B.; Hosken, G. D.; Stanbury, T. V. Tetrahedron. 2001, 57, 9635–9648. DOI: https://doi.org/10.1016/S0040-4020(01)00964-4
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. DOI: https://doi.org/10.1016/S0968-0896(99)00185-6
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. DOI: https://doi.org/10.1021/ja00198a089
18. Tietze, L. F.; Vob, E. Tetrahedron Lett.1986, 27, 6181–6184. DOI: https://doi.org/10.1016/S0040-4039(00)85427-1
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. DOI: https://doi.org/10.1021/jo9604907
21. Aumann, R.; Gotlkrr-Schnetmann, I.; Frotlich, R.; Enketo, P. S.; Holst, C. Chemistry–A European Journal. J. 2001, 7, 711–720. DOI: https://doi.org/10.1002/1521-3765(20010202)7:3<711::AID-CHEM711>3.0.CO;2-5
22. Michael, J. P. Pure and applied chemistry. 1997, 69, 583–588. DOI: https://doi.org/10.1351/pac199769030583
23. Martin, D. F.; Janusonis, G. A.; Martin, B. B. Journal of the American Chemical Society. 1961, 83, 73–75. DOI: https://doi.org/10.1021/ja01462a015
24. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis. 1983, 11, 902–903. DOI: https://doi.org/10.1055/s-1983-30557
25. Kouadri, Y., Ouahrani, M. R., Missaoui, B. E., Chebrouk, F., & Gherraf, N. Asian Journal of Chemistry. 2015, 27(10), 3676. DOI: https://doi.org/10.14233/ajchem.2015.18918
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 DOI: https://doi.org/10.1016/j.tetlet.2003.12.093
28. Khodaei, M. M.; Khosropour, A. R.; Kookhazadeh, M. Synlett. 2004, 1980–1984. DOI: https://doi.org/10.1055/s-2004-830879
29. Lenin, R.; Madhusudhan R., R. Arkivoc. 2007, XIII, 204–209. DOI: https://doi.org/10.3998/ark.5550190.0008.d23
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. DOI: https://doi.org/10.1021/jo01303a003
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. DOI: https://doi.org/10.1039/b210165c
34. Zhang, Z. H.; Hu, J. Y. Journal of the Brazilian Chemical Society. 2006, 17, 1447–1451. DOI: https://doi.org/10.1590/S0103-50532006000700038
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. DOI: https://doi.org/10.1016/j.molcata.2006.04.065
36. Masoumeh, M., Farhad, S., Mohadeseh, S., Masoumeh, M. Polycyclic Aromatic Compounds. doi: 10.1080/10406638.2018.1454967. DOI: https://doi.org/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 DOI: https://doi.org/10.9767/bcrec.14.3.4574.551-558
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. DOI: https://doi.org/10.9767/bcrec.11.3.578.376-388
41. Kherroub, D. E., Belbachir, M., Lamouri, S. Bulletin of Chemical Reaction Engineering & Catalysis. 2014, 9 (1):74-80 DOI: https://doi.org/10.9767/bcrec.9.1.5555.74-80
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. DOI: https://doi.org/10.1016/j.reactfunctpolym.2006.07.006
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.
