One-pot efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-triaryl-1H-imidazoles using oxalic acid catalyst

Synthesis

Volumn , Issue 18, 2007, Pages 2829-2834

  Kokare, Nagnnath D ^a,b   Sangshetti, Jaiprakash N ^a   Shinde, Devanand B ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

^b New Drug Discovery   (India)

Author keywords

2,4,5 triaryl 1H imidazole; 2 aryl 1 arylmethyl 1H benzimidazole; Aromatic aldehydes; Benzil; Benzoin; Oxalic acid

Indexed keywords

BENZIL; BENZOIN; OXALIC ACID;

ALDEHYDES; CARBOXYLIC ACIDS; CATALYSTS; ETHANOL; SOLVENTS;

AROMATIC COMPOUNDS;

1,2 PHENYLENEDIAMINE; 2 ARYL 1 ARYLMETHYL 1H BENZIMIDAZOLE DERIVATIVE; 2,4,5 TRIARYL 1H IMIDAZOLE DERIVATIVE; ALDEHYDE; BENZIMIDAZOLE DERIVATIVE; BENZOIN; IMIDAZOLE DERIVATIVE; OXALIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34948893906     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983872     Document Type: Article

References (52)

1. (a) Tamm, I.; Sehgal, P. B. Adv. Virus Res. 1978, 22, 187.
2. (b) Tamm, I. Science 1957, 126, 1235.
3. (c) Tebbe, M. J.; Spitzer, W. A.; Victor, F.; Miller, S. C.; Lee, C. C.; Sattelberg, T. R. Sr.; McKinney, E.; Tang, J. C. J. Med. Chem. 1997, 40, 3937.
4. (d) Migawa, M. T.; Giradet, J. L.; Walker, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1998, 41, 1242.
5. (e) Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1998, 41, 1252.
6. (a) Grimmett, M. R. Imidazole and Benzimidazole Synthesis; Acadamic Press: San Diego, 1997.
7. (b) Roth, M.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W. Jr.; Michejda, C. J. J. Med. Chem. 1997, 40, 4199.
8. Figge, A.; Altenbach, H. J.; Brauer, D. J.; Tielmann, P. Tetrahedron: Asymmetry 2002, 13, 137.
9. (a) Dudd, L. M.; Venardou, E.; Gaircia-Verdugo, E.; Licence, P.; Blake, A. J.; Wilson, C.; Poliakoff, M. Green Chem. 2003, 5, 187.
10. (b) Preston, P. N. In The Chemistry of Heterocyclic Compounds, Vol. 40; Weissberger, A.; Taylor, E. C., Eds.; John Wiley: New York, 1981.
11. (c) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665.
12. (d) Chi, Y.-C.; Sun, C.-M. Synlett 2000, 591.
13. (e) Bougrin, K.; Soufiaoui, M. Tetrahedron Lett. 1995, 36, 3683.
14. (a) Perry, R. J.; Wilson, B. D. J. Org. Chem. 1993, 58, 7016.
15. (b) Brain, C. T.; Brunton, S. A. Tetrahedron Lett. 2002, 43, 1893.
16. (c) Konig, W.; Gieger, R. Chem. Ber. 1970, 103, 788.
17. (a) Sun, W. H.; Shao, S. H.; Chen, Y.; Hu, H. M.; Sheldon, R. A.; Wang, H. G.; Leng, X. B.; Jin, X. L. Organometallics 2002, 21, 4350.
18. (b) Ben-alloum, A.; Bakkas, S.; Soufiaoui, M. Tetrahedron Lett. 1998, 39, 4481.
19. (a) Nagata, K.; Itoh, T.; Ishikawa, H.; Ohsawa, A. Heterocycles 2003, 61, 93.
20. (b) Currini, M.; Epifana, F.; Montanari, F.; Rosati, O.; Taccone, S. Synlett 2004, 1832.
21. Wilfred, C. D.; Taylor, R. J. K. Synlett 2004, 1628.
22. (a) Kim, B. H.; Han, R.; Kim, J. S.; Jun, Y. M.; Baik, W.; Lee, B. M. Heterocycles 2004, 63, 41.
23. (b) Yang, D. L.; Fokas, D.; Li, J. Z.; Yu, L. B.; Baldino, C. M. Synthesis 2005, 47.
24. (a) Kokare, N. D.; Nagawade, R. R.; Rane, V. P.; Shinde, D. B. Synthesis 2007, 766.
25. (b) Kotharkar, S. A.; Jadhav, M. R.; Nagawade, R. R.; Bahekar, S. S.; Shinde, D. B. Lett. Org. Chem. 2005, 2, 398.
26. (c) Nagawade, R. R.; Khanna, V. V.; Bhagwat, S. S.; Shinde, D. B. Eur. J. Med. Chem. 2005, 40, 1325.
27. (d) Bahekar, S. S.; Shinde, D. B. Tetrahedron Lett. 2004, 45, 7999.
28. (e) Bahekar, S. S.; Kotharkar, S. A.; Shinde, D. B. Mendeleev Commun. 2004, 210.
29. (a) Smith, A. B. III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Korn, A. Org. Synth. Coll. Vol. VII; John Wiley & Sons: London, 1990, 271.
30. (b) Meyers, A. I.; Flanagan, M. E. Org. Synth. Coll. Vol. IX; John Wiley & Sons: London, 1998, 258.
31. (c) Politzer, I. R.; Meyers, A. I. Org. Synth Coll. Vol. VI; John Wiley & Sons: London, 1988, 905.
32. Fieser, L. F. Org. Coll. Vol. IV; John Wiley & Sons: London, 1963, 195.
33. Apelian, M. R.; Fung, A. S.; Kennedy, G. J.; Degnan, T. F. J. Phys. Chem. 1996, 100, 16577.
34. (a) Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S. R. Tetrahedron Lett. 2007, 48, 69.
35. (b) Peipei, S.; Zhixin, H. J. Heterocycl. Chem. 2006, 43, 773.
36. (a) Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, N.; Heys, J. R.; Landvatter, S. W.; Streckler, J. E.; McLaugher, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, J. P.; White, J. R.; Adams, J. L.; Young, P. R. Nature 1994, 372, 739.
37. (b) Maier, T.; Schmierer, R.; Bauer, K.; Bieringer, H.; Buerstell, H.; Sachse, B. US 4,820,335, 1989; Chem. Abstr. 1989, 111, 19494.
38. (c) Schierer, R.; Mildenberger, H.; Buerstell, H. DE 3614364, 1987; Chem. Abstr. 1988, 108, 37838.
39. (a) Wasserscheid, P.; Keim, W. Angew Chem. Int. Ed. 2000, 39, 37872.
40. (b) Bourissou, D.; Guerret, O.; Ggabbai, F. T.; Bertrand, G. Chem. Rev. 2000, 100.
41. (a) Balalaie, S.; Arabanian, A.; Hashtroudi, M. S. Monatsh. Chem. 2000, 131, 945.
42. (b) Hayes, J. F.; Mitchell, M. B.; Wicks, C. Heterocycles 1994, 38, 575.
43. (c) Lozinskaya, N. A.; Tsybezova, V. V.; Proskurnina, M. V.; Zefirov, N. S. Russ. Chem. Bull. 2003, 52, 674.
44. (a) Weiss, M.; Abbel, M. J. Am. Chem. Soc. 1948, 70, 3666.
45. (b) McKillop, A.; Swann, B.; Ford, M. E.; Taylor, E. C. J. Am. Chem. Soc. 1973, 95, 3641.
46. (c) Zhang, G. S.; Shi, Q. Z.; Chen, M. F.; Cai, K. Synth. Commun. 1997, 27, 953.
47. (a) Siddiqui, S. A.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivason, K. V. Tetrahedron 2005, 61, 3539.
48. (b) Kidwai, M.; Mothsra, P.; Bansal, V.; Goyal, R. Monatsh. Chem. 2006, 137, 1189.
49. Subba Rao, N. V.; Ratnam, C. V. Curr. Sci. 1955, 24, 9199.
50. Puaschkina, L. N.; Mazalov, S. A.; Postovskii, I. Y. Zh. Obsch. Khim. 1962, 32, 2624.
51. Subba Rao, N. V.; Ratnam, C. V. Proc Indian Acad. Sci., Sect. A 1956, 43, 173.
52. Perumal, S.; Mariappan, S.; Sevaraj, S. ARKIVOC 2004, (viii), 46.