One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols

Tetrahedron Letters

Volumn 52, Issue 43, 2011, Pages 5571-5574

  Raghavendra, Goravanahalli M ^a   Ramesha, Ajjahalli B ^a   Revanna, Cigalli N ^a   Nandeesh, Kebbahalli N ^a   Mantelingu, Kempegowda ^a   Rangappa, Kanchugarakoppal S ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

T3P; Benzimidazole; Benzothiazole; o Aminothiophenols; o Diaminoarenes

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 AMINOTHIOPHENOL; ACETIC ACID ETHYL ESTER; ACID ANHYDRIDE; ALCOHOL DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; DIMETHYL SULFOXIDE; PROPYLPHOSPHONIC ANHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; DEHYDROGENATION; ONE POT SYNTHESIS; OXIDATION; REACTION OPTIMIZATION; REACTION TIME; TEMPERATURE;

EID: 80053207188     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.037     Document Type: Article

References (44)

1. F.A. Tanious, D. Hamelberg, C. Bailly, A. Czarny, D.W. Boykin, and W.D. Wilson J. Am. Chem. Soc. 126 2004 143
2. T.C. Kuhler, M. Swanson, V. Shcherbuchin, H. Larsson, B. Mellgard, and J.E. Sjostrom J. Med. Chem. 41 1998 1777
3. A. Mavrova, K.K. Anichina, D.I. Vuchev, J.A. Tsenov, P.S. Denkova, M.S. Kondeva, and M.K. Micheva Eur. J. Med. Chem. 41 2006 1412
4. Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada, and T. Naka J. Med. Chem. 39 1996 5228
5. W.W. Mederski, D. Dorsch, S. Anzali, J. Gleitz, B. Cezanne, and C. Tsaklakidis Bioorg. Med. Chem. Lett. 14 2004 3763
6. M.L. Richards, S.C. Lio, A. Sinha, K.K. Tieu, and J.C. Sircar J. Med. Chem. 47 2004 6451
7. G.I. Elmer, J.O. Pieper, S.R. Goldberg, and F.R. George Psychopharmacology (Berl.) 117 1995 23
8. M. Mader, A. de Dios, C. Shih, and B.D. Anderson Bioorg. Med. Chem. Lett. 18 2008 179
9. F. Arjmand, B. Mohani, and S. Ahmad Eur. J. Med. Chem. 40 2005 1103
10. F. Gualtieri, G. Brody, A.H. Fieldsteel, and W.A. Skinner J. Med. Chem. 15 1972 420
11. J. Valdez, R. Cedillo, A. Hernandez-Campos, L. Yepez, F. Hernandez-Luis, G. Navarrete-Vazquez, A. Tapia, R. Cortes, M. Hernandez, and R. Castillo Bioorg. Med. Chem. Lett. 12 2002 2221
12. I. Tamm Science 126 1957 1235
13. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, and L.B. Townsend J. Med. Chem. 41 1998 1251
14. M.R. Grimmett Imidazole and Benzimidazole Synthesis 1997 Academic Press San Diego
15. K.R. Hornberger, G.M. Adjabeng, H.D. Dickson, and R.G. Davis-Ward Tetrahedron Lett. 47 2006 5359
16. R. Wang, X.X. Lu, X.Q. Yu, L. Shi, and Y. Sun J. Mol. Catal. A: Chem. 266 2007 198
17. C. Mukhopadhyay, and P.K. Tapaswi Tetrahedron Lett. 49 2008 6237
18. C. Lin, P.T. Lai, S.K.S. Liao, W.-T. Hung, W.-B. Yang, and J.-M. Fang J. Org. Chem. 73 2008 3848
19. D. Yang, D. Fokas, J. Li, L. Yu, and C.M. Baldino Synthesis 2005 47
20. C.M. Surpur, P.R. Singh, S.B. Patil, and S.D. Samant Synth. Commun. 37 2007 1375
21. B. Zou, Q. Yuan, and Ma Angew. Chem., Int. Ed. 46 2007 2598
22. G. Evindar, and R.A. Batey Org. Lett. 5 2003 133
23. M. Curini, and F. Epifano Synlett 2004 1832
24. C.D. Wilfred, and R.J.K. Taylor Synlett 2004 1628
25. V.R. Ruiz, A. Corma, and M.J. Sabater Tetrahedron Lett. 66 2010 730
26. T. Kondo, S. Yang, K.T. Huh, M. Kobayashi, S. Kotachi, and Y. Watanabe Chem. Lett. 1991 1275
27. J.W. Kim, J. He, K. Yamaguchi, and N. Mizuno Chem. Lett. 62 2009 1275
28. A.J. Blacker, M.M. Farah, M.I. Hall, S.P. Marsden, O. Saidi, and J.M. Williams Org. Lett. 11 2009 2039
29. J.N. Moorthy, and I. Neogi Tetrehedron Lett. 52 2011 3868
30. B. Plumb, and D.J. Harper Chem. Eng. News 1990 3
31. S. Chandrappa, K. Vinaya, C.S. Ananda Kumar, and K.S. Rangappa Tetrhedron Lett. 51 2010 6493
32. G.M. Raghavendra, K.B. Harsha, K. Vinaya, K. Mantelingu, and K.S. Rangappa Synth. Commun. 41 2011 2296
33. Revanna, C. N.; Swaroop, T. R.; Raghavendra, G. M.; Bhadre Gowda, D. G.; Mantelingu, K.; Rangappa, K. S.; J. Heterocycl. Chem. in press, doi:00880.
34. S. Chandrappa, K. Vinaya, T. Ramakrsihanappa, and K.S. Rangappa Synlett 20 2010 3019
35. A.L. Llanes Garcia Synlett 2007 1328
36. F. Burkhart, M. Hoffmann, and H. Kessler Angew. Chem., Int. Ed. 36 1997 1191
37. F.L. Zumpe, F. Melanie, K. Schmitz, and A. Lender Tetrahedron Lett. 48 2007 1421
38. J.K. Augustine, R.N. Atta, B.K. Ramappa, and C. Boodappa Synlett 2009 3378
39. J.K. Augustine, V. Vairaperumal, S. Narasimhan, P. Alagarsamy, and A. Radhakrishnan Tetrahedron 65 2009 9989
40. M. James, J.M. Crawforth, and M. Paoletti Tetrahedron Lett. 50 2009 4916
41. N.N. Basavaprabhu, S.L. Ravi, and V.V. Sureshbabu Tetrehedron. Lett. 51 2010 3002
42. Meudt, A.; Scherer. S.; Böhm, C. PCT Int. Appl. WO 2005102978, 2005.
43. Chem. Abstr. 2005, 143, 440908.
44. J.K. Augustine, V.V. Sharmila, N.P. Alagarsamy, and A. Radhakrishnan Tetrahedron 65 2009 9989