Regioselective Friedel-Crafts alkylation of indoles with epoxides using nano MgO

Green Chemistry Letters and Reviews

Volumn 5, Issue 3, 2012, Pages 439-449

  Hosseini Sarvari, Mona ^a   Parhizgar, Golnaz ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

epoxide; Friedel Crafts alkylation; indole; nano MgO; solvent free

Indexed keywords

CATALYST; MAGNESIUM; OXIDE; REACTION RATE; STOICHIOMETRY;

EID: 84868245715     PISSN: 17518253     EISSN: 17517192     Source Type: Journal    
DOI: 10.1080/17518253.2012.666273     Document Type: Article

References (57)

1. Li, J.T.; Dai, H.G.; Lin, Z.P. Prog. Chem. 2007, 19, 751-761.
2. Tomioka, Y.; Ohkubo, K.; Maruoka, H.J. Heterocycl. Chem. 2007, 44, 419-424.
3. Unaleroglu, C.; Aytac, S.; Temelli, B. Heterocycles 2007, 71, 2427-2440.
4. Huffman, J.W.; Padgett, L.W.; Isherwood, M.L.; Wiley, J.L.; Martin, B.R. Bioorg. Med. Chem. Lett. 2006, 16, 5432-5435.
5. Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 8, 1199-1222.
6. Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484-1485.
7. Saracoglu, N. Top. Heterocycl. Chem. 2007, 11, 1-61
8. Bandini, M.; Melloni, A.; Umani-Ronchi, A. Org. Lett. 2004, 6, 3199-3202.
9. Jorapur, Y.R.; Lee, C.-H.; Chi, D.Y. Org. Lett. 2005, 7, 1231-1236.
10. Yadav, J.S.; Reddy, B.V.S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 8331-8334.
11. Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 7160-7163.
12. Palomo, C.; Oiarbide, M.; Kardak, B.G.; Garcia, J.M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154-4155.
13. Lin, C.; Hsu, J.; Sastry, M.N.V.; Fang, H.; Tu, Z.; Liu, J.-T.; Ching-Fa, Y. Tetrahedron 2005, 61, 11751-11757
14. Azizi, N.; Arynasab, F.; Saidi, M.R. Org. Biomol. Chem. 2006, 4, 4275-4277.
15. Bandini, M.; Cozzi, P.G.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 5386-5389.
16. Zou, X.; Wang, X.; Cheng, C.; Kong, L.; Mao, H. Tetrahedron Lett. 2006, 47, 3767-3771.
17. Lin, S.; You, T. Tetrahedron 2009, 65, 1010-1016.
18. Tabatabaeian, K.; Mamaghani, M.; Mahmoodi, N.O.; Khorshidi, A. Tetrahedron Lett. 2008, 49, 1450-1454.
19. Das, B.; Thirupathi, P.; Kumar, R.A.; Reddy, K.R. Catal. Commun. 2008, 9, 635-638.
20. Liu, Y.H.; Liu, Q.S.; Zhang, Z.H. Tetrahedron Lett. 2009, 50, 916-921.
21. Azizi, N.; Mehrazma, S.; Saidi, M.R. Can. J. Chem. 2006, 84 5, 800-803.
22. Heydari, A.; Mehrdad, M.; Maleki, A.; Ahmadi, N. Synthesis 2004, 10, 1557-1558.
23. Yadav, J.S.; Reddy, B.V.S.; Parimala, G. J. Chem. Res. Synop. 2003, 2, 78-81.
24. Westermaier, M.; Mayr, H. Chem. Eur. J. 2008, 14, 1638-1647.
25. Kotsuki, H.; Teraguchi, M.; Shimomoto, N.; Ochi, M. Tetrahedron Lett. 1996, 37, 3727-3730.
26. Yadav, J.S.; Reddy, B.V.S.; Araham, S.; Sabitha, G. Synlett 2002, 9, 1550-1552.
27. Bandini, M.; Cozzi, P.G.; Melchiorre, P.; Ronchi, A.U. J. Org. Chem. 2002, 67, 5386-5389.
28. Bandgar, B.P.; Patil, A.V. Tetrahedron Lett. 2007, 48, 173-176.
29. Hudlicky, T.; Rinner, U.; Finn, K.J.; Ghiviriga, I. J. Org. Chem. 2005, 70, 3490-3499.
30. Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. 1996, 61, 984-990.
31. Kotsuki, H.; Nishiuchi, M.; Kobayashi, S.; Nishizawa, H. J. Org. Chem. 1990, 55, 2969-2972.
32. Kantam, M.L.; Chakravarti, R.; Sreedhar, B.; Bhargava, S. Synlett 2008, 10, 1449-1454.
33. Michalkova, A.; Ilchenko, M.; Gorb, L.; Leszczynski, J. J. Phys. Chem. B 2004, 108, 5294-5303.
34. Kantam, M.L.; Laha, S.; Yadav, J.; Sreedhar, B. Tetrahedron Lett. 2006, 47, 6213-6217.
35. Anders, M.W.; Jakobson, I. Scand. J. Work Environ. Health 1985, 11 1, 23-32.
36. Bolt, H.M.; Borlak, J.T. In Toxicology; Marquardt, H. Academic Press 1999, Medical, Chapter 26 645-654.
37. Kumar, D.; Reddy, V.B.; Mishra, B.G.; Rana, R.K.; Nadagouda, M.N.; Varma, R.S. Tetrahedron 2007, 63, 3093-3097.
38. Yu, J.C.; Xu, A.; Zhang, L.; Song, R.; Wu, L. J. Phys. Chem. B 2004, 108 1, 64-70.
39. Li, Y.X.; Klabunde, K.J. Langmuir 1991, 7 7, 1388-1393.
40. Lu, H.B.; Liao, L.; Li, H.; Tian, Y.; Li, J.C.; Wang, D.F.; Zhu, B.P. J. Phys. Chem. C 2007, 111 28, 10273-10277.
41. Richards, R.; Li, W.; Decker, S.; Davidson, C.; Koper, O.; Zaikovski, V.; Volodin, A.; Rieker, T.; Klabunde, K.J. J. Am. Chem. Soc. 2000, 122 20, 4921-4928
42. Zhou, Q.; Yang, J.W.; Wang, Y.Z.; Wu, Y.H.; Wang, D.Z. Mater. Lett. 2008, 62, 1887-1897.
43. J. Hu, K. Zhu, L. Chen, C. Kbel, R. Richards, J. Phys. Chem. C 2007, 111 32, 12038-12044.
44. Stark, J.V.; Klabunde, K.J. Chem. Mater. 1996, 8 8, 1913-1918.
45. Hosseini-Sarvari, M.; Sharghi, H. J. Iran. Chem. Soc. 2008, 5, 384-393.
46. Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652-6654
47. Hosseini-Sarvari, M.; Etemad, S. Tetrahedron 2008, 64, 5519-5523.
48. Hosseini-Sarvari, M.; Sodagar, E.; Doroodmand, M.M. J. Org. Chem. 2011, 76, 2853-2859
49. Hosseini-Sarvari, M. Catalysis Lett. 2011, 114, 347-355.
50. Hosseini-Sarvari, M. Chin. Chem. Lett. 2011, 22, 547-554.
51. Hosseini-Sarvari, M. J. Iran. Chem. Soc. 2011, 8, s119-s128.
52. Hosseini-Sarvari, M.; Safary, E. J. Sulfur Chem. 2011, 37, 463-473.
53. Niu, H.; Yang, Q.; Tang, K.; Xie, Y. Scripta Materialia 2006, 54, 1791-1725.
54. Culity, B.D. Elements of X-Ray Diffraction; New York: Addison-Wesley, 1978 1.
55. Snyder, L.R. J. Chromatography A, 1967, 28, 300-316
56. Drexler, M.T.; Amiridis, M.D. J. Catal. 2003, 214, 136-145.
57. Yoshihiko, I. Bull. Chem. Soc. Jpn. 1984, 57, 73-84.