Copper(I)-catalyzed synthesis of substituted 2-mercapto benzimidazoles

Journal of Organic Chemistry

Volumn 74, Issue 5, 2009, Pages 2217-2220

  Murru, Siva ^a,b   Patel, Bhisma K ^b   Le Bras, Jean ^a   Muzart, Jacques ^a  

^a UFR des Sciences Exactes et Naturelles   (France)

^b INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE; BENZIMIDAZOLES; CATALYZED SYNTHESIS; COPPERS (I); EFFICIENT METHODS; HIGH YIELDS; N-ARYLATION; P-METHOXYBENZYL; SHORT REACTION TIME; THIONES;

HYDROCARBONS; SYNTHESIS (CHEMICAL); THIOUREAS;

UREA;

2 (4 METHOXYBENZYLTHIO) 1 PHENYLBENZIMIDAZOLE; 2 (METHYLTHIO) 1 (FURAN 2 YLMETHYL)BENZIMIDAZOLE; 2 (METHYLTHIO) 1 4 TOLYLBENZIMIDAZOLE; 2 (METHYLTHIO) 1 BENZYLBENZIMIDAZOLE; 2 (METHYLTHIO) 1 PHENYLBENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; CUPROUS ION; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; ARYLATION; DRUG STRUCTURE; DRUG SYNTHESIS;

BENZIMIDAZOLES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 64249105656     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802589d     Document Type: Article

References (53)

1. Saluja, S.; Zou, R.; Urach, J. C.; Townsend, L. B. J. Med. Chem. 1996, 39, 881.
2. Kosano, H.; Kayanuma, T.; Nishigori, H. Biochem. Biophys. Acta 2000, 1499, 11.
3. Tatsuta, M.; Kataoka, M.; Yasoshima, K.; Sakakibara, S.; Shogase, Y.; Shimazaki, M.; Yura, T.; Li, Y.; Yamamoto, N.; Guptab, J.; Urbahns, K. Bioorg. Med. Chem. Lett. 2005, 15, 2265.
4. (a) Corban, G. J.; Hadjikakou, S. K.; Hadjiliadis, N.; Kubicki, M.; Tiekink, E. R. T.; Butler, I. S.; Drougas, E.; Kosmas, A. M. Inorg. Chem. 2005, 44, 8617.
5. (b) Doerge, D. R.; Decker, C. J.; Takazawa, R. S. Biochemistry 1993, 32, 58.
6. (a) Tomić, M.; Ignjatović, D.; Tovilović. G.; Andrić. D.; Roglić, G.; Kostić-Rajačić, S. Bioorg. Med. Chem. Lett. 2007, 17, 5749.
7. (b) Andrić, D.; Tovilvić, G.; Roslić, G.; Soškić, V.; Tomić, M.; Kostić-Rajačić, S. J. Serb. Chem. Soc. 2007, 72, 747.
8. (a) Seenivasaperumal, M.; Federsel, H.-J.; Ertan, A.; Szabó, K. J. Chem. Commun. 2007, 2187.
9. (b) Vidaillac, C.; Guillon, J.; Arpin, C.; Forfar-Bares, I.; Ba, B. B.; Grellet, J.; Moreau, S.; Caignard, D.-H.; Jarry, C.; Quentin, C. Antimicrob. Agents Chemother. 2007, 51, 831.
10. (c) Shin, J. M.; Cho, Y. M.; Sachs, G. J. Am. Chem. Soc. 2004, 126, 7800.
11. (a) Lan, P.; Romero, F. A.; Malcolm, T. S.; Stevens, B. D.; Wodka, D.; Makara, G. M. Tetrahedron Lett. 2008, 49, 1910.
12. (b) Teague, S. J.; Barber, S.; King, S.; Stein, L. Tetrahedron Lett. 2005, 46, 4613.
13. (c) Gupta, R. P.; Larroquette, C. A.; Agrawal, K. C. J. Med. Chem. 1982, 25, 1342.
14. (a) Hwu, J. R.; Singha, R.; Hong, S. C.; Chang, Y. H.; Das, A. R.; Vliegen, I.; De Clereq, E.; Neyts J. Antivir. Res. 2008, 77, 157.
15. (b) Mavrova, A. Ts.; Anichina, K. K.; Vuchev, D. I.; Tsenov, J. A.; Denkova, P. S.; Kondeva, M. S.; Micheva, M. K Eur. J. Med. Chem. 2006, 41, 1412.
16. (c) Mavrova, A. Ts.; Anichina, K K: Vuchev, D. I.; Tsenov, J. A.; Kondevad, M. S.; Micheva, M. K. Bioorg. Med. Chem. 2005, 13, 5550.
17. (d) Roy, A. D.; Sharma, S.; Grover, R. K.; Kundu, B.; Roy, R. Org. Lett. 2004, 6, 4163.
18. (e) Andrzejewska, M.; Yépez-Mulia, L.; Cedillo-Rivera, R.; Tapia, A.; Vilpo, L.; Vilpo. J.; Kazimierczuk, Z. Eur. J Med. Chem. 2002, 37, 973.
19. (f) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2002, 12, 2221.
20. (g) Klimešová, V.; Kočí, J.; Pour, M.; Stachel, J.; Waisser, K.; Kaustová, J. Eur. J. Med. Chem. 2002, 37, 409.
21. (h) Wright, J. B. Chem. Rev. 1951, 48. 397.
22. Zhang, P.; Terefenko, E. A.; Wrobel, J.; Zhang, Z,: Zhu, Y.; Cohen, J.; Marschke, K. B.; Mais, D. Bioorg. Med. Chem. Lett. 2001, 11, 2747.
23. (a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
24. (b) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096.
25. (c) Chemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153.
26. (d) Beletskava, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
27. Minatti, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721.
28. Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968.
29. Zheng, N.; Buchwald, S. L. Org. Lett. 2007, 9, 4749.
30. Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761.
31. Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337.
32. Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598.
33. Zou, B.; Yuan, Q.; Ma, D. Org. Lett. 2007, 9, 4291.
34. (a) Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett. 2008, 10, 625.
35. (b) Chen. Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329.
36. (c) Liu, F.; Ma, D. J. Org. Chem. 2007, 72, 4844.
37. Yuan, Q.; Ma, D. J. Org. Chem. 2008, 73, 5159.
38. (a) Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452.
39. (b) Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
40. Evindar, G.; Batev, R. A. Org. Lett. 2003, 5, 133.
41. (a) Murru. S.; Singh, C. B.; Kavala, V.; Patel. B. K. Tetrahedron 2008, 64, 1931.
42. (b) Yella, R.; Ghosh. H.; Patel, B. K. Green Chem. 2008, 10, 1307.
43. (c) Singh, C. B.; Murru, S.; Kavala, V.; Patel, B. K. Org. Lett. 2006, 8, 5397.
44. (a) Wang, J.; Peng, F.; Jiang, J.-I.; Lu, Z.-j.; Wang, L.-y.; Bai, J.; Pan, Y. Tetrahedron Lett. 2008, 49, 467.
45. (b) Joyce, L. L.; Evindar, G.; Batey, R. A. Chem. Commun. 2004, 446.
46. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. 2nd ed.; Wiley: New York. 1991.
47. (b) Holler. T. P.; Spaltenstein, A.; Turner, E.; Klevit, R. E.; Shapiro, B. M.; Hopkins, P. B. J. Org. Chem. 1987, 52, 4420.
48. (c) Sakabori, S.; Sakakibara, S.; Shimonishi, Y.; Nobuhara, Y. Bull. Chem. Soc. Jpn. 1964, 37, 433.
49. Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S.; Wu, Y.-Q. Org. Lett. 2005, 7, 2429.
50. Soural, M.; Bouillon. I.; Krchňák, V. J. Comb. Chem. 2008, 10, 923.
51. Benzimidazole thiones have two tautomeric forms and can be drawn as either thioenol or as thione. It is believed that these compounds exist primarily in the thione form. Therefore, for the purposes of this publication, we will refer to and draw the products as thiones. For discussions on the tautomerism of thiones, see: (a) Khan, H.; Badshah, A.; Shaheen, F.; Gieck, C.; Qureshi, R. A. Acta Crystallogr. 2008, E64, o1141.
52. (b) Öǧretir, C.; Öztürk, İ. İ.; Tay, N. F. Arkivoc 2007, 14, 75.
53. (c) Elzbieta, B.-O.; Lech, S.; Graham, A. W.; Ian, H. S. Bull Pol. Acad. Sci., Chem. 1987, 35, 81.