An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water

Tetrahedron Letters

Volumn 47, Issue 1, 2006, Pages 79-82

  Gogoi, Pranjal ^a   Konwar, Dilip ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

Benzimidazole; Imidazoline; Iodine and potassium iodide in water; Oxidation; Water media

Indexed keywords

ALDEHYDE; BENZIMIDAZOLE DERIVATIVE; CARBON; DIAMINE; IMIDAZOLINE DERIVATIVE; NITROGEN; WATER;

ANAEROBIC METABOLISM; ARTICLE; CHEMICAL BOND; COST EFFECTIVENESS ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; TEMPERATURE;

EID: 28544451672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.134     Document Type: Article

References (44)

1. M.R. Grimmett A.R. Katrizky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry Vol. 3 1996 Pergamon Oxford 77 220
2. J.V. Greenhill, and L. Lue G.P. Ellis D.K. Luscombe Progress in Medicinal Chemistry Vol. 3 1993 Elsevier New York
3. P.N. Preston Chem. Rev. 74 1974 279 314
4. F. Touzeau, A. Arrault, G. Guillaumet, E. Scalbert, B. Pfeiffer, M.-C. Rettori, P. Renard, and J.-Y. Merour J. Med. Chem. 46 2003 1962 1979
5. F. Rondu, G.L. Bihan, X. Wang, A. Lamouri, E. Touboul, G. Dive, T. Bellahsene, B. Pfeiffer, P. Renard, B. Guardiola-Lemaitre, D. Manechez, L. Penicaud, A. Ktorza, and J.-J. Godfroid J. Med. Chem. 40 1997 3793 3803
6. R.C.F. Jones, and J.R. Nichols Tetrahedron Lett. 31 1990 1771 1774
7. R.C.F. Jones, M.J. Smallridge, and C.B. Chapleo J. Chem. Soc., Perkin Trans. 1 1990 385 391
8. T. Hayashi, E. Kishi, V.A. Soloshonok, and Y. Uozumi Tetrahedron Lett. 37 1996 4969 4972
9. Y.-R. Lin, X.-T. Zhou, L.-X. Dai, and J. Sun J. Org. Chem. 62 1997 1799 1803
10. Y. Hsiao, and L.S. Hegedus J. Org. Chem. 62 1997 3586 3591
11. M.E. Jung, and A. Huang Org. Lett. 2 2000 2659 2661
12. R.C.F. Jones, I. Turner, and K.J. Howard Tetrahedron Lett. 34 1993 6329 6332
13. Y. Langlois, and P.I. Dalko J. Org. Chem. 63 1998 8107 8117
14. R.C.F. Jones, K.J. Howard, and J.S. Snaith Tetrahedron Lett. 37 1996 1707 1710
15. E.J. Corey, and M.J. Grogan Org. Lett. 1 1999 157 160
16. T. Isober, K. Fukuda, Y. Araki, and T. Ishikawa Chem. Commun. 2001 243 244
17. C. Botteghi, A. Schionato, G. Chelucci, H. Brunner, A. Kurzinger, and U. Obermann J. Organomet. Chem. 370 1989 17 31
18. T. Morimoto, K. Tachibana, and K. Achiwa Synlett 1997 783 785
19. A.J. Davinport, D.L. Davies, J. Fawcett, and D.R. Russell J. Chem. Soc., Perkin Trans. 1 2001 1500 1503
20. F. Menges, M. Neuburger, and A. Pfaltz Org. Lett. 4 2002 4713 4716
21. N.A. Boland, M. Casey, S.J. Hynes, J.W. Matthews, H. Muller-Bunz, and P. Wilkes Org. Biomol. Chem. 2 2004 1995 2002
22. P.N. Preston, M.F.G. Stevens, and G. Tennant Benzimidazoles and Congeneric Tricyclic Compounds, Part 2 1980 John Wiley & Sons New York
23. R. Cedillo-Rivera, and O. Munoz J. Med. Microbiol. 37 1992 221 224
24. B. Chavez, R. Cedillo-Rivera, and A. Martiner-Palomo J. Protozool. 39 1992 510 515
25. G. Navarrete-Vazquez, R. Cedillo, A. Hernandez-Campos, L. Yepez, F. Hernandez-Luis, J. Valdez, R. Morales, R. Cortes, M. Hernandez, and R. Castillo Bioorg. Med. Chem. Lett. 11 2001 187 190
26. G. Neef, U. Eder, and G. Sauer J. Org. Chem. 46 1981 2824 2826
27. B. George, and E.P. Papadopoulos J. Org. Chem. 42 1977 441 443
28. H. Fujioka, K. Murai, Y. Ohba, A. Hiramatsu, and Y. Kita Tetrahedron Lett. 46 2005 2197 2199
29. S. Peddibhotla, and J.J. Tepe Synthesis 2003 1433 1440
30. D.H. Huh, H. Ryu, and Y.G. Kim Tetrahedron 60 2004 9857 9862
31. J.M. Mitchell, and N.S. Finney Tetrahedron Lett. 41 2000 8431 8434
32. S.-L. You, and J.W. Kelly Org. Lett. 6 2004 1681 1683
33. L.A. Paquette Encyclopedia of Reagents for Organic Synthesis Vol. 4 1995 John Wiley & Sons New York 2796
34. P. Gogoi, G.K. Sarma, and D. Konwar J. Org. Chem. 69 2004 5153 5154
35. P. Gogoi, P. Hazarika, and D. Konwar J. Org. Chem. 70 2005 1935 1936
36. R.N. Leyden, M.S. Loonat, W.E. Neuse, B.H. Sher, and W.J. Watkinson J. Org. Chem. 48 1983 727 731
37. 2 (0.75 mmol) was added portionwise over 5 min, and the mixture was heated at 90°C with stirring for the stipulated time (Table 1). Sodium thiosulfate solution (10 ml; 5%) was added and the product was extracted with ethyl acetate (15 ml × 3). The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by crystallization or column chromatography (silica gel) using hexane and ethyl acetate as eluent.
38. +) 196.335, found 196.324.
39. P.H. Svensson, and L. Kloo Chem. Rev. 103 2003 1649 1684
40. F.E. Scully Jr., and R.C. Davis J. Org. Chem. 43 1978 1467 1468
41. P. Oxley, and W.F. Short J. Chem. Soc. 1947 497
42. H.M. Woodburn, and R.C. O'Gee J. Org. Chem. 17 1952 1235 1244
43. C.J. Pouchert 2nd ed. The Aldrich Library of NMR Spectra Vol. 2 1983
44. Dictionary of Organic Compounds 6th ed. 1996 Chapman and Hall London