Diastereoselective synthesis of novel 2,5-dioxopyrrolidine derivatives via biocatalytic domino reactions

: A series of novel 2,5-dioxopyrrolidines were synthesized by the one-pot reaction of coumarin-3-carboxylic acids 1 with thiourea derivatives and alkyl isocyanides in the presence of Fe 3 O4 NPs @ lipase as heterogeneous reusable nanobiocatalysts with high yields.

PDF

___

1. Obniska, J.; Zagorska, A. Il Farmaco 2003, 58, 1227-1234.
2. Malawska, B. Curr. Top. Med. Chem. 2005, 5, 69-85.
3. Imamura, S.; Ishihara, Y.; Hattori, T.; Kurasawa, O.; Matsushita, Y.; Sugihara, Y.; Kanzaki, N.; Iizawa, Y.; Baba, M.; Hashiguchi, S. Chem. Pharm. Bull. 2004, 52, 63-73.
4. Li, X.; Li, Y.; Xu, W. Bioorg. Med. Chem. 2006, 14, 1287-1293.
5. Barrett, D. G.; Catalano, J. G. D.; Deaton, N.; Hassell, A. M.; Long, S.T.; Miller, A. B.; Miller, L. R.; Ray, J. A.; Samano, V.; Shewchuk, L. M. et al. Bioorg. Med. Chem. Lett. 2006, 16, 1735-1739.
6. Tran, J. A.; Chen, C. W.; Jiang, W.; Tucci, F. C.; Fleck, B. A.; Marinkovic, D.; Arellano, M.; Chen, C. Bioorg. Med. Chem. Lett. 2007, 17, 5165-5170.
7. Lokhande, T. N.; Bobade, A. S.; Khadse, B. G. Indian Drugs 2003, 40, 147-150.
8. Hensler, M. E.; Bernstein, G.; Nizet, V.; Nefzi, A. Bioorg. Med Chem Lett. 2006, 16, 5073-5079.
9. D¨onda¸s, H. A.; Nural, Y.; Duran, N.; Kilner, C. Turk. J. Chem. 2006, 30, 573-583.
10. Colandrea, V. J.; Legiec, I. E.; Huo, P.; Yan, L.; Hale, J. J.; Mills, S. G.; Bergstrom, J.; Card, D.; Chebret, G.; Hajdu, R. et al. Bioorg. Med. Chem. Lett. 2006, 16, 2905-2908.
11. Yan, L.; Budhu, R.; Huo, P.; Lynch, C. L.; Hale, J. J.; Mills, S. G.; Hajdu, R.; Keohane, C. A.; Rosenbach, M. J.; Milligan, J. A. et al. Bioorg. Med. Chem. Lett. 2006, 16, 3564-3568.
12. Baharfar, R.; Azimi, R.; Barzegar, S.; Mohseni, M. J. Braz. Chem. Soc. 2015, 26, 1396-1404.
13. Baharfar, R.; Asghari, S.; Peiman, S. Arabian J. Chem. (in press).
14. Baharfar, R.; Azimi, R. J. Chem. Sci. 2015, 127, 1389-1395.
15. Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
16. Zhu, J. Eur. J. Org. Chem. 2003, 7, 1133-1144.
17. Ulaczyk-Lesanko, A.; Hall, D. G. Curr. Opin. Chem. Biol. 2005, 9, 266-276.
18. Domling, A. Chem. Rev. 2006, 106, 17-89.
19. Tejedor, D.; Garc´ıa-Tellado, F. Chem. Soc. Rev. 2007, 36, 484-491.
20. Akbarzadeh, R.; Amanpour, T.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2014, 70, 169-175.
21. Muller, M. Adv. Synth. Cat. 2012, 354, 3161-3174.
22. Xu, F.; Wang, J. L.; Liu, B. K.; Wu, Q.; Lin, X. F. Green Chem. 2011, 13, 2359-2361.
23. Li, C.; Feng, X. W.; Wang, N.; Zhou, Y. J.; Yu, X. Q. Green Chem. 2008, 10, 616-618.
24. Xie, B. H.; Guan, Z.; He, Y. H. J. Chem. Technol. Biotech. 2012, 87, 1709-1714.
25. He, Y. H.; Hu, W.; Guan, Z. J. Org. Chem. 2012, 77, 200-207.
26. Guan, Z.; Fu, J. P.; He, Y. H. Tet. Lett. 2012, 53, 4959-4961.
27. Li, C.; Feng, X. W.; Wang, N.; Zhou, Y. J.; Yu, X. Q. Green Chem. 2008, 10, 616-618.
28. Zheng, J.; Xie, B. H.; Chen, Y. L.; Cao, J. F.; Yang, Y.; Guan, Z.; He, Y. H. Z. Naturforsch. C 2014, 69, 170-180.
29. Wang, J. L.; Liu, B. K.; Yin, C.; Wu, Q.; Lin, X. F. Tetrahedron 2011, 67, 2689-2692.
30. Li, K.; He, T.; Li, C.; Feng, X. W.; Wang, N.; Yu, X. Q. Green Chem. 2009, 11, 777-779.
31. Xie, Z. B.; Wang, N.; Jiang, G. F.; Yu, X. Q. Tetrahedron Let. 2013, 54, 945-947.
32. Wu, W. B.; Wang, N.; Xu, J. M.; Wu, Q.; Lin, X. F. Chem. Comm. 2005, 18, 2348-2350.
33. Baharfar, R.; Mohajer, S. Helv. Chim. Acta 2012, 95, 185-190.
34. Baharfar, R.; Asghari, S.; Zaheri, F.; Shariati, N. Comt. Rend. Chimie 2016 (in press).
35. Baharfar, R.; Shariati, N. Turk. J. Chem. 2015, 39, 235-243.
36. Baharfar, R.; Mohajer, S. Catal. Lett. 2016, 146, 1729-1742.
37. Shaabani, A.; Soleimani, E.; Rezayan, A. H.; Sarvary, A.; Khavasi, H. R. Org. Lett. 2008, 10, 2581-2584.
38. Ugi, I.; Steinbruckner, C. Chem. Ber. 1961, 94, 2802-2814.
39. Mossetti, R.; Saggiorato, D.; Tron, G. C. J. Org. Chem. 2011, 76, 1025-10262.
40. Bora, P. P.; Bihani, M.; Bez, G. J. Mol. Catal. B-Enzym. 2013, 92, 24-33.
41. Xu, J. C.; Li, W. M.; Zheng, H.; Lai, Y. F.; Zhang, P. F. Tetrahedron 2011, 67, 9582-9587.
42. Liang, Y. R; Chen, X. Y.; Wu, Q., Lin, X. F. Tetrahedron 2015, 71, 616-621.
43. Znabet, A.; Polak, M. M.; Janssen, E.; de Kanter, F. J. J.; Turner, N. J.; Orru, R. V. A.; Ruijter, E. Chem. Comm. 2010, 46, 7918-7920.
44. Schnell, B.; Krenn, W.; Faber, K.; Kappe, C. O. J. Chem. Soc. Per. Tr. 2000, 1, 4382-4389.