Isoprene-catalyzed lithiation of imidazole: Synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles

Tetrahedron

Volumn 61, Issue 47, 2005, Pages 11148-11155

  Torregrosa, Rosario ^a   Pastor, Isidro M ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Carbonyl compounds; Deprotonation; Imidazole; Imines; Isoprene catalyzed lithiation

Indexed keywords

IMIDAZOLE DERIVATIVE; IMINE; ISOPRENE; LITHIUM;

ARTICLE; CATALYSIS; CRYSTALLIZATION; DRUG SYNTHESIS; LITHIATION; PRIORITY JOURNAL; ROOM TEMPERATURE; STOICHIOMETRY;

EID: 27144549639     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.024     Document Type: Article

References (61)

1. M.R. Grimmet A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 3 1996 Pergamon Oxford 77 220
2. M.R. Grimmett Sci. Synth. 12 2002 325 528
3. C.A. Zificsak, and D.J. Hlasta Tetrahedron 60 2004 8991 9016
4. For reviews see, for instance: (a) B.H. Lipshutz Chem. Rev. 86 1986 795 820
5. R. Chinchilla, C. Nájera, and M. Yus Chem. Rev. 104 2004 2667 2722
6. B. Iddon Heterocycles 23 1985 417 443
7. B. Iddon, and R.I. Ngochindo Heterocycles 38 1994 2487 2568
8. A.R. Katritzky, G.W. Rewcastle, and W.Q. Fan J. Org. Chem. 53 1988 5685 5689
9. M.D. Cliff, and S.G. Pyne Tetrahedron 52 1996 13703 13712
10. S. Ohta, M. Matsukawa, N. Ohashi, and K. Nagayama Synthesis 1990 78 81
11. N.S. Mani, J.A. Jablonowski, and T.K. Jones J. Org. Chem. 69 2004 8115 8117
12. G. Shapiro, and B. Gomez-Lor J. Org. Chem. 59 1994 5524 5526
13. J. Winter, and J. Retey Synthesis 1994 245 246
14. R.I. Ngochindo J. Chem. Soc., Perkin Trans. 1 1990 1645 1648
15. D.A. Goff, G.A. Koolpe, A.B. Kelson, H.M. Vu, D.L. Taylor, C.D. Bedford, R.N. Harris III, H.A. Mussalam, and I. Koplovitz J. Med. Chem. 34 1991 1363 1368
16. A.R. Katritzky, J.J. Slawinski, F. Brunner, and S. Gorun J. Chem. Soc., Perkin Trans. 1 1989 1139 1145
17. M. Moreno-Mañas, J. Bassa, N. Llado, and R. Pleixats J. Heterocycl. Chem. 27 1990 673 678
18. A. Hassner, P. Munger, and B.A. Belinka Jr. Tetrahedron Lett. 23 1982 699 702
19. Z. Jin Nat. Prod. Rep. 20 2003 584 605
20. C.A. Zificsak, and D.J. Hlasta Tetrahedron Lett. 46 2005 4789 4792
21. For reviews, see: (a) M. Yus Chem. Soc. Rev. 25 1996 155 161
22. D.J. Ramón, and M. Yus Eur. J. Org. Chem. 2000 225 237
23. M. Yus Synlett 2001 1197 1205
24. M. Yus, and D.J. Ramón Lat. J. Chem. 2002 79 92
25. D.J. Ramón, and M. Yus Rev. Cubana Quim. 14 2002 75 115
26. M. Yus Z. Rappoport I. Mareck The Chemistry of Organolithium Compounds Vol. 1 2004 Wiley Chichester 647 747 Chapter 11
27. For reviews, see: (a) C. Nájera, and M. Yus Trends Org. Chem. 2 1991 155 181
28. C. Nájera, and M. Yus Org. Prep. Proced. Int. 27 1995 383 457
29. C. Nájera, and M. Yus Recent Res. Dev. Org. Chem. 1 1997 67 96
30. M. Yus, and F. Foubelo Rev. Heteroat. Chem. 17 1997 73 107
31. C. Nájera, and M. Yus Curr. Org. Chem. 7 2003 867 926
32. C. Nájera, J.M. Sansano, and M. Yus Tetrahedron 59 2003 9255 9303
33. (g) Ref. 4b.
34. R. Chinchilla, C. Nájera, and M. Yus Tetrahedron 61 2005 3139 3176
35. (i) See also the special issue of Tetrahedron Symposium-in-Print dedicated to 'Functionalised Organolithium Compounds'; Tetrahedron 2005, 61, 3125-3450 (Guest editors: Najera, C.; Yus, M.).
36. M. Yus, and F. Foubelo P. Knochel Functionalised Organometallics 2005 Wiley-VCH Weinheim Chapter 2
37. For a review on the generation of organolithium compounds starting from non-halogenated precursors, see: D. Guijarro, and M. Yus Recent Res. Dev. Org. Chem. 2 1998 713 744
38. For reviews, see: (a) Ref. 17d.
39. M. Yus, and F. Foubelo O.A. Attanasi D. Spinelli Targets in Heterocyclic Systems Vol. 6 2002 Italian Society of Chemistry Rome 136 171
40. M. Yus Pure Appl. Chem. 75 2003 1453 1475
41. For reviews, see: (a) F. Foubelo, and M. Yus Trends Org. Chem. 7 1998 1 26
42. F. Foubelo, and M. Yus Curr. Org. Chem. 9 2005 459 490
43. I.M. Pastor, and M. Yus Tetrahedron Lett. 41 2000 5335 5339
44. I.M. Pastor, and M. Yus Tetrahedron Lett. 42 2001 1029 1032
45. M. Yus, R. Torregrosa, and I.M. Pastor Molecules 9 2004 330 348
46. See, for instance: A. De Nicola, J. Einhorn, and J.-L. Lucke J. Chem. Res. (S) 1991 278
47. Lischka, U.; Hauk, D.; Rittmeyer, P.; Wietelmann, U. German Patent 19849197, 2000; Chem. Abstr. 2000, 132, 137554.
48. S.Y. Kim, G.-I. An, and H. Rhee Synlett 2003 112 114
49. A. Hirao, I. Hattori, K. Yamaguchi, and S. Nakahama Synthesis 1982 461 462
50. D.J. Hart, K. Nakai, G. Thomas, and T.-K. Yang J. Org. Chem. 48 1983 289 294
51. G. Cainelli, and M. Panunzio J. Am. Chem. Soc. 110 1988 6879 6880
52. F. Foubelo, C. Gómez, A. Gutiérrez, and M. Yus J. Heterocycl. Chem. 37 2000 1061 1064
53. D.A. Shirley, and P.W. Alley J. Am. Chem. Soc. 79 1957 4922 4927
54. I. Kawasaki, T. Osaki, K. Tsunoda, E. Watanabe, M. Matsuyama, A. Sanai, A. Khadeer, M. Yamashita, and S. Ohta Tetrahedron 60 2004 6639 6648
55. S. Ohta, T. Yamamoto, I. Kawasaki, M. Yamashita, Y. Nagashima, and T. Yoshikawa Chem. Pharm. Bull. 42 1994 821 825
56. D. Yijun, and D.J. Hlasta Tetrahedron Lett. 43 2002 189 192
57. S. Ohta, S. Hayakawa, K. Nishimura, and M. Okamoto Tetrahedron Lett. 25 1984 3251 3254
58. N.A. Ross, R.R. MacGregor, and R.A. Bartsch Tetrahedron 60 2004 2035 2041
59. M.A. Vazquez, M. Landa, L. Reyes, R. Miranda, J. Tamariz, and F. Delgado Synth. Commun. 34 2004 2705 2718
60. J.H. Hartley, M.D. Phillips, and T.D. James New J. Chem. 26 2002 1228 1237
61. D. Yijun, and D.J. Hlasta Org. Lett. 4 2002 4017 4020