l-Proline catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles

Tetrahedron Letters

Volumn 48, Issue 1, 2007, Pages 69-72

  Varala, Ravi ^a   Nasreen, Aayesha ^a   Enugala, Ramu ^a   Adapa, Srinivas R ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZIMIDAZOLE; CHLOROFORM; PROLINE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; SUBSTITUTION REACTION;

EID: 33751419514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.010     Document Type: Article

References (64)

1. Tebbe M.J., Spitzer W.A., Victor F., Miller S.C., Lee C.C., Sattelberg T.R., Mckinney E., and Tang C.J. J. Med. Chem. 40 (1997) 3937-3946
2. Porcari A.R., Devivar R.V., Kucera L.S., Drach J.C., and Townsend L.B. J. Med. Chem. 41 (1998) 1252-1262
3. Roth M., Morningstar M.L., Boyer P.L., Hughes S.H., Bukheit R.W., and Michejda C.J. J. Med. Chem. 40 (1997) 4199-4207
4. Migawa M.T., Giradet J.L., Walker J.A., Koszalka G.W., Chamberlain S.D., Drach J.C., and Townsend L.B. J. Med. Chem. 41 (1998) 1242-1251
5. Tamm I., and Seghal P.B. Adv. Virus Res. 22 (1978) 187-258
6. Tamm I. Science 126 (1957) 1235-1236
7. Kim J.S., Gatto B., Yu C., Liu A., Liu L.F., and Lavioe E. J. Med. Chem. 39 (1996) 992-998
8. Zarrinmayeh H., Zimmerman D.M., Cantrell B.E., Schober D.A., and Bruns R.F. Bioorg. Med. Chem. Lett. 9 (1999) 647-652
9. Kohara Y., Kubo K., Imamiya E., Wada T., Inada Y., and Naka T. J. Med. Chem. 39 (1996) 5228-5235
10. Lopez M.L.R., Benhamu B., Morcillio M.J., Tejada I.D., Orensanz L., Alfaro L., and Martin M.I. J. Med. Chem. 33 (1990) 814-819
11. Forseca T., Gigante B., and Gilchrist T.L. Tetrahedron 57 (2001) 1793-1799 and references cited therein
12. Zhao J., Arnaiz D., Griedel B., Sakata B., Dallas J., Whitlow M., Trinh L., Post J., Liang A., Morrissey M., and Shaw K. Bioorg. Med. Chem. Lett. 10 (2000) 963-966
13. Stevenson C., Davies R., and Jeremy H. Chem. Res. Toxicol. 12 (1999) 38-45
14. Mason J.S., Morize I., Menard P.R., Cheney D.L., Hume C., and Labaudiniere R.F. J. Med. Chem. 42 (1999) 3251-3264
15. Preston P.N. In: Weissberger A., and Taylor E.C. (Eds). Chemistry of Heterocyclic Compounds Vol. 40 (1981), John Wiley and Sons
16. Chi Y.-C., and Sun C.-M. Synlett (2000) 591-594
17. Huang W., and Scarborough R.M. Tetrahedron Lett. 40 (1999) 2665-2668
18. Dudd L.M., Venardou E., Garcia-Verdugo E., Licence P., Blake A.J., Wilson C., and Poliakoff M. Green Chem. 5 (2003) 187-192
19. Wu Z., Rea P., and Wickam G. Tetrahedron Lett. 41 (2000) 9871-9874 and references cited therein
20. Mazurov A. Bioorg. Med. Chem. Lett. 10 (2000) 67-70
21. Kim B.H., Han R., Kim J.S., Jun Y.M., Baik W., and Lee B.M. Heterocycles 63 (2004) 41-54
22. Itoh T., Nagata K., Ishikawa H., and Ohsawa A. Heterocycles 63 (2004) 2769-2783
23. Tumelty D., Cao K., and Holmes C.P. Org. Lett. 3 (2001) 83-86
24. Kilburn J.P., Lau J., and Jones R.C.F. Tetrahedron Lett. 41 (2000) 5419-5421 and references cited therein
25. Pertry R.J., and Wilson B.D. J. Org. Chem. 58 (1993) 7016-7021
26. Esser F., Ehrengart P., and Ignanatow H.P. J. Chem. Soc., Perkin Trans. 1 (1999) 1153-1154
27. Anastasiou D., Campi E.M., Chaouk H., and Jackson W.R. Tetrahedron 48 (1992) 7467-7468
28. Brain C.T., and Brunton S.A. Tetrahedron Lett. 43 (2002) 1893-1895
29. Perumal S., Mariappan S., and Selvaraj S. Arkivoc viii (2004) 46-51
30. Salehi P., Dabiri M., Zolfigol M.A., Otokesh S., and Baghbanzadeh M. Tetrahedron Lett. 47 (2006) 2557-2560
31. Sun P., and Hu Z. J. Heterocycl. Chem. 43 (2006) 773-775
32. List B. Tetrahedron 58 (2002) 5573-5590
33. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580-591
34. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
35. Lacoste E. Synlett 12 (2006) 1973-1974 and references cited therein
36. Wang Y., Shang Z.-c., Wu T.-x., Fan J.-c., and Chen X. J. Mol. Catal. A: Chem. 253 (2006) 212-221
37. Srinivasan M., Perumal S., and Selvaraj S. Arkivoc xi (2005) 201-208
38. Kotrusz P., and Toma S. Molecules 11 (2006) 197-205
39. Yadav J.S., Kumar S.P., Kondaji G., Rao R.S., and Nagaiah K. Chem. Lett. 33 (2004) 1168-1169
40. Sabitha G., Fatima N., Reddy E.V., and Yadav J.S. Adv. Synth. Catal. 347 (2005) 1353-1355
41. Shen Z., Li B., Wang L., and Zhang Y. Tetrahedron Lett. 46 (2005) 8785-8788
42. Dodda R., and Zhao C.-G. Synthesis 19 (2006) 3238-3242
43. Varala R., Ramu E., Sreelatha N., and Adapa S.R. Tetrahedron Lett. 47 (2006) 877-880 and references cited therein
44. Varala R., and Adapa S.R. Org. Proc. Res. Dev. 9 (2005) 853-856
45. Varala R., Sreelatha N., and Adapa S.R. Synlett 10 (2006) 1549-1553
46. Varala R., Ramu E., Sreelatha N., and Adapa S.R. Synlett 7 (2006) 1009-1012
47. Varala R., Ramu E., and Adapa S.R. Synthesis 22 (2006) 3825-3830
48. Varala R., Ramu E., Kumar P.V., and Adapa S.R. Chin. J. Chem. 24 (2006) 807-810
49. Varala R., Sreelatha N., and Adapa S.R. Bull. Korean Chem. Soc. 27 (2006) 1079-1082
50. Alam M.M., Varala R., Ramu E., and Adapa S.R. Lett. Org. Chem. 3 (2006) 187-190
51. Varala R., Ramu E., and Adapa S.R. Bull. Chem. Soc. Jpn. 79 (2006) 140-141
52. Varala R., Sreelatha N., and Adapa S.R. J. Org. Chem. 71 (2006) 8283-8286
53. 2: C, 84.48; H, 5.67; N, 9.85. Found: C, 84.34; H, 5.69; N, 9.78.
54. Bahmanyar S., Houk K.N., Matin H.J., and List B. J. Am. Chem. Soc. 125 (2003) 2475-2479
55. Arno M., and Domingo L.R. Theor. Chem. Acc. 108 (2002) 232-239
56. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 12911-12912
57. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 11273-11283
58. Groger H., and Wilken J. Angew. Chem., Int. Ed. 40 (2001) 529-532
59. Sekiguchi Y., Sasaoka A., Shimomoto A., Fujioka S., and Kotsuki H. Synlett (2003) 1655-1658
60. List B., Pojarliev P., and Castello C. Org. Lett. 4 (2001) 573-575
61. Li G.-l., and Zhao G. J. Org. Chem. 70 (2005) 4272-4278
62. Borah B.M., and Das G. Tetrahedron Lett. 47 (2006) 3135-3138
63. Yanagisawa A., Nakamura Y., and Arai T. Tetrahedron: Asymmetry 15 (2004) 1909-1913
64. Varala, R.; Ramu, E.; Adapa, S. R., unpublished results.