L-Proline as an efficient catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles

Bulletin of the Korean Chemical Society

Volumn 30, Issue 9, 2009, Pages 1963-1966

  Shitole, Nana V ^a   Shelke, Kiran F ^a   Sonar, Swapnil S ^a   Sadaphal, Sandip A ^a   Shingate, Bapurao B ^a   Shingare, Murlidhar S ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

2,4,5 triaryl substituted imidazoles; Ammonium acetate; Aromatic aldehydes; Benzil; L Proline

Indexed keywords

AMMONIUM ACETATE; AROMATIC ALDEHYDE; EFFICIENT CATALYSTS; L-PROLINE; ONE-POT SYNTHESIS; ORGANOCATALYSTS; SHORT REACTION TIME;

ALDEHYDES; AROMATIC COMPOUNDS; PLANTS (BOTANY); SYNTHESIS (CHEMICAL);

AMMONIUM COMPOUNDS;

EID: 75649083097     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.9.1963     Document Type: Article

References (55)

1. Lambardino, J.G.; Wiseman, E.H. J. Med. Chem. 1974, 17, 1182.
2. Brimblecombe, R.W.; Duncan, W.A.M.; Durant, G.J.; Emmett, J.C.; Ganellin, C.R.; Parons, M.E. J. Int. Med. Res. 1975, 3, 386.
3. Tanigawara, Y.; Aoyama, N.; Kita, T.; Shirakawa, K.; Komada, F.; Kasuga, M.; Okumura, K. Clin Pharmacol. Ther. 1999, 66, 528.
4. Heers, J.; Backx, L.J.J.; Mostmans, J.H.; Van Custsem, J. J. Med. Chem. 1979, 22, 1003.
5. Wasserscheid, P.; Keim, W. Angew Chem. Int. Ed. 2000, 39, 37872.
6. Bourissou, D.; Guerret, O.; Ggabbai, F.T.; Bertrand, G. Chem. Rev. 2000, 100.
7. Satoru, I. Jap. Pat. 1989, 01, 117, 867, Chem. Abstr. 1989, 111, 214482.
8. Radziszewski, B. Chem. Ber. 1882, 15, 1493.
9. Grimmett, M.R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C.W.; Scriven, E.F.V., Eds.; Pergamon: New York, 1996, 3, 77.
10. Balalaie, S.; Arabanian, A.; Hashtroudi, M.S. Mont. Fur. Chem. 2000, 131, 945.
11. Sharam, G.V.M.; Jyothi, Y.; Lakshimi, P.S. Synth. Commun. 2006, 36, 2991.
12. Heravi, M.M.; Bakhtiari, K.; Oskooie, H.A.; Taheri, S. J. Mol. Catal. A: Chem. 2007, 263, 279.
13. Siddiqui, S.A.; Narkhede, U.G.; Palimkar, S.S.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Tetrahedron 2005, 61, 3539.
14. Kidwai, M.; Mothsra, P.; Bansal, V.; Goyal, R. Mont. Fur. Chem. 2006, 137, 1189.
15. Sangshetti, J.N.; Kokare, N.D.; Kothakar, S.A.; Shinde, D.B. Mont. Fur. Chem. 2008, 139, 125.
16. Grimmett, M.R. In Comperhensive Hetercyclic Chemistry; Kattritzky, A.R.; Rees, C.W., Eds.; Pergamon: New York, 1984, 5, 457.
17. Wolkenberg, S.E.; Winoski, D.D.; Leister, W.H.; Wang, Y.; Zhao, Z.; Lindsley, C.W. Org. Lett. 2004, 6, 1453.
18. Kidwai, M.; Saxena, S.; Ruby.; Rastogi, S. Bull. Korean Chem. Soc. 2005, 26, 2051.
19. Wang, L.W.; Wang, Y.H.; Tian, H.; Yao, Y.F.; Shao, J.H.; Liu, B. J. Fluorine Chem. 2006, 127, 1570.
20. Khodaei, M.M.; Bahrami, K.; Kavianinia, I.J. J. Chin. Chem. Soc. 2007, 54, 829.
21. Mohammadi1, A. A.; Mivechi, M.; Kefayati, H. Monatsh Chem. 2008, 139, 935.
22. Sharma, S.D.; Hazarika, P.; Konwar, D. Tetrahedron Letters 2008, 49, 2216.
23. Mizuno, N.; Misono, M. Chem. Rev. 1998, 98, 199.
24. Notz, W.; Tanaka, F.; Barbas, C.F., III. Acc. Chem. Res. 2004, 37, 580.
25. Dalko, P.I.; Moisan, L. Angew. Chem, Int. Ed. 2004, 43, 5138.
26. Lacoste, E. Synlett 2006, 12, 1973.
27. Wang, Y.; Shang, Z.C.; Wu, T.X.; Fan, J.C.;Chen, X. J. Mol. Catal. A: Chem. 2006, 253, 212.
28. Srinivasan, M.; Perumal, S.; Selvaraj, S. Arkivoc 2005, xi, 201.
29. Sabitha, G.; Fatima, N.; Reddy, E.V.; Yadav, J.S. Adv. Synth. Catal. 2005, 347, 1353.
30. Dodda, R.; Zhao, C.G. Synthesis 2006, 19, 3238.
31. Varala, R.; Ramu, E.; Sreelatha, N.; Adapa, S.R. Tetrahedron Lett. 2006, 476, 877;.
32. Varala, R.; Adapa, S.R. Org. Proc. Res. Dev. 2005, 9, 853.
33. An, Z.; Zhang, W.: Shi, H.; He, J. Journal of Catalysis 2006, 241, 319-327.
34. Karade, N.N.; Budhewar, V.H.; Shinde, S.V.; Jadhav, W.N. Lett. in Org. Chem. 2007, 4, 16.
35. Sadaphal, S.A.; Markhele, V.M.; Sonar, S.S.; Shingare, M.S. J. Korean Chemical Soc. 2008, 52, 454.
36. Pawar, S.S.; Dekhane, D.V.; Shingare, M.S.; Thore, S.N. Tetrahedron Lett. 2008, 49, 4252.
37. Sadaphal, S.A.; Shelke, K.F.; Sonar, S.S.; Shingare, M.S. Central Euro. J. Chem. 2008, 6, 622.
38. Sonar, S.S.; Kategaonkar, A.H.; Ware, M.N.; Gill, C.H.; Shingate, B.B.; Shingare, M.S. Arkivoc 2009, ii, 138.
39. Shelke, K.F.; Sapkal, S.B.; Sonar, S.S.; Madje, B.R.; Shingate, B.B.; Shingare, M.S. Bull. Korean Chem. Soc. 2009, 30, 1057.
40. Li, G.I.; Zhao, G. J. Org. Chem. 2005, 70, 4272.
41. Borah, B.M.; Das, G. Tetrahedron Lett. 2006, 47, 3135.
42. Yanagisawa, A.; Nakamura, Y.; Arai, T. Tetrahedron: Asymmetry 2004, 15, 1909.
43. Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S.R. Tetrahedron Lett. 2007, 48, 69.
44. Bahmanyar, S.; Houk, K.N.; Matin, H.J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475.
45. Arno, M.; Domingo, L.R. Theor. Chem. Acc. 2002, 108, 232.
46. Bahmanyar, S.; Houk, K.N. J. Am. Chem. Soc. 2001, 123, 12911.
47. Bahmanyar, S.; Houk, K.N. J. Am. Chem. Soc. 2001, 123, 11273.
48. Grogee, H.; Wilken, J. Angew. Chew. Int. Ed. 2001, 40, 529.
49. List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
50. Sharma, S.D.; Hazarika, P.; Konwar, D. Tetrahedron Lett. 2008, 49, 2216.
51. 6, 400 MHz, δ ppm): 7.6-8.1 (m, 15 H, Ar-H), 12.50 (1 H, brs, NH). ES-MS (m/z): 297 (M + 1).
52. 6, 400 MHz, δ ppm): 3.90 (s, 3 H), 7.05 (d, 2 H, J = 8.4 Hz, Ar-H), 7.90 (d, 2 H, J = 8.4 Hz, Ar-H). 7.30-7.80 (m, 10 H, Ar-H), 12.21 (1 H, brs, NH). ES-MS (m/z): 327 (M + 1).
53. 6, 400 MHz, δ ppm): 7.35 (d, 2 H, J = 8.4 Hz, Ar-H), 7.85 (d, 2 H, J = 8.4 Hz, Ar-H) 7.20-7.70 (m, 10 H, Ar-H) 12.16 (1 H, brs, NH). ES-MS (m/z): 331 (M + 1), 332 (M + 3).
54. 6, 400 MHz, δ ppm): 7.90 (d, 2 H, J = 8.4 Hz, Ar-H), 8.2 (d, 2 H, J = 8.4, Ar-H) 7.15-7.70 (m, 10 H, Ar-H) 12.10 (1 H, brs, NH). ES-MS (m/z): 342 (M + 1).
55. 6, 400 MHz, δ ppm): 11.21 (brs, 1 H, NH), 7.15-7.6 (m, 10 H, Ar-H) 7.46-7.58 (m, 4 H). ES-MS (m/z): 287 (M + 1).