Alkylation of the ambident indole ion in ionic liquids

Chemistry of Heterocyclic Compounds

Volumn 44, Issue 5, 2008, Pages 530-541

  Vavilina, G ^a   Zicmanis, A ^a   Drozdova, S ^a   Mekss, P ^a   Klavins, M ^a  

^a UNIVERSITY OF LATVIA   (Latvia)

Author keywords

Alkylation; Ambident anion; Indole; Ionic liquids

Indexed keywords

EID: 66149108499     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-008-0072-y     Document Type: Article

References (44)

1. M. J. Earle, P. B. McCormac, and K. R. Seddon, J. Chem. Soc., Chem. Commun., 2245 (1998).
2. Z.-G. Le, Z.-C. Chen, Y. Hu, and Q.-G. Zheng, Synthesis, 2, 208 (2004).
3. Y. R. Jorapur, J. M. Jeong, and D. Y. Chi, Tetrahedron Lett., 47, 2435 (2006).
4. M. J. Earle, P. B. McCormac, and K. R. Seddon, Green Chem., 2, 261 (2000).
5. A. Zicmanis, G. Vavilina, S. Drozdova, P. Mekss, and M. Klavins, Central Eur. J. Chem., 5, 156 (2007).
6. A. Zicmanis, A. Ozolina, P. Mekss, and M. Klavins, Latv. J. Chem., 141 (2006).
7. A. Zicmanis, G. Vavilina, S. Drozdova, M. Klavins, and P. Mekss, Latv. J. Chem., 301 (2006).
8. A. Zicmanis, G. Vavilina, M. Klavins, and P. Mekss, Latv. J. Chem., 172 (2007).
9. G. V. Kryshtal, G. M. Zhdankina, and S. G. Zlotin, Mendeleev Commun., 57 (2002).
10. M. Badri, J.-J. Brunet, and R. Perron, Tetrahedron Lett., 33, 4435 (1992).
11. G. Shao, Hecheng Huaxue, 11, 6 (2003);
12. Chem. Abs., 139, 116960 (2003).
13. D. R. MacFarlane, J. M. Pringle, K. M. Johansson, S. A. Forsyth, and M. Forsyth, J. Chem. Soc., Chem. Commun., 1905 (2006).
14. J. Dupont, C. S. Consorti, and J. Spencer, J. Brazil. Chem. Soc., 11, 337 (2000).
15. S. T. Handy, Curr. Org. Chem., 9, 959 (2005).
16. N. Jain, A. Kumar, S. Chauhan, and S. M. S. Chauhan, Tetrahedron, 61, 1015 (2005).
17. Z.-B. Zhou, H. Matsumoto, and K. Tatsumi, Chem. Eur. J., 11, 752 (2005).
18. G. W. Meindersma, A. J. G. Podt, and A. B. De Haan, Fuel Processing Technology, 87, 59 (2005).
19. C. Baudequin, D. Bregeon, J. Levillain, F. Guillen, J.-C. Plaquevent, and A.-C. Gaumont, Tetrahedron: Asymmetry, 16, 3921 (2005).
20. K. N. Marsh, J. A. Boxall, and R. Lichtenthaler, Fluid Phase Equilibria, 219, 93 (2004).
21. C. F. Poole, J. Chromatogr. A, 1037, 49 (2004).
22. P. Kubisa, Prog. Polym. Sci., 29, 3 (2004).
23. C. E. Song, J. Chem. Soc., Chem. Commun., 1033 (2004).
24. P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, VCH, Weinheim (2003).
25. M. A. Abraham and L. Moens, Clean Solvents: Alternative Media for Chemical Reactions and Processing, ACS Symposium Series 819, ACS, Washington DC (2002).
26. R. Sheldon, J. Chem. Soc., Chem. Commun., 2399 (2001).
27. P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed. Engl., 39, 3772 (2000).
28. R. D. Rogers and K. R. Seddon, Ionic Liquids: Industrial Application to Green Chemistry, ACS Symposium Series 818, ACS, Washington DC (2002).
29. T. Welton, Chem. Rev., 99, 2071 (1999).
30. V. I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007).
31. L. M. Kustov, T. V. Vasina, and V. A. Ksenofontov, Ros. Khim. Zh., 43, 13 (2004).
32. S. Chowdhury, R. S. Mohan, and J. L. Scott, Tetrahedron, 63, 2363 (2007).
33. S. Nunomoto, Y. Kawakami, Y. Yamashita, H. Takeuchi, and S. Eguchi, J. Chem. Soc., Perkin Trans. 1, 111 (1990).
34. M. G. Reinecke, J. F. Sebastian, H. W. Johnson, Jnr., and C. Pyun, J. Org. Chem., 37, 3066 (1972).
35. B. Cardillo, G. Casnati, A. Pochini, and A. Ricca, Tetrahedron, 23, 3771 (1967).
36. R. Gompper, Usp. Khim., 36, 803 (1967).
37. S. A. Shevelev, Usp. Khim., 39, 1773 (1970).
38. G. Pirson and J. Songstad, J. Am. Chem. Soc., 89, 1817 (1967).
39. R. Gompper, Angew. Chem., Int. Ed. Engl., 15, 321 (1976).
40. C. Reichardt, Green Chem., 7, 339 (2005).
41. C. Reichardt, Chem. Rev., 94, 2319 (1994).
42. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser, and R. D. Rogers, J. Chem. Soc., Chem. Commun., 1765 (1998).
43. T. Nishida, Y. Tashiro, and M. Yamamoto, J. Fluorine Chem., 120, 135 (2003).
44. C. S. Cho, H. S. Shim, H.-J. Choi, T.-J. Kim, and S. C. Shim, Bull. Korean Chem. Soc., 25, 441 (2004).