Synthesis of 1,3,5-trisubstituted-1,2,4-triazoles by microwave-assisted N-acylation of amide derivatives and the consecutive reaction with hydrazine hydrochlorides

Tetrahedron

Volumn 68, Issue 8, 2012, Pages 2045-2051

  Lee, Jongbok ^a   Hong, Myengchan ^a   Jung, Yoonchul ^a   Cho, Eun Jin ^a   Rhee, Hakjune ^a  

^a Hanyang University   (South Korea)

Author keywords

1,2,4 Triazole; Cyclization reaction; Microwave assisted reaction; N Acylation reaction; One pot sequential reaction

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; AMIDE; BENZAMIDE; HYDRAZINE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICROWAVE RADIATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 84862783584     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.003     Document Type: Article

References (31)

1. Y.A. Al-Soud, M.N. Al-Dweri, and N.A. Al-Masoudi Farmaco 59 2004 775
2. N. Demirbas, R. Ugurluoglu, and A. Demirbas Bioorg. Med. Chem. 10 2002 3717
3. B. Tozkoparan, N. Gokhan, G. Aktay, E. Yesilada, and M. Ertan Eur. J. Med. Chem. 35 2000 743
4. S. Conde, C. Corral, and R. Madronero Synthesis 1974 28
5. W. Su, D. Yang, and J. Li Synth. Commun. 35 2005 1435
6. K. Paulvannan, T. Chen, and R. Hale Tetrahedron 56 2000 8071
7. K. Paulvannan, R. Hale, D. Sedehi, and T. Chen Tetrahedron 57 2001 9677
8. B.I. Buzykin, and Z.A. Bredikhina Synthesis 1993 59
9. S. Caddik Tetrahedron 51 1995 10403
10. P. Lidstrom, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225
11. N. Jagerovic, L. Hernandez-Folgado, I. Alkorta, P. Goya, M. Navarro, A. Serrano, F.R. Fonseca, M.T. Dannert, A. Alsasua, M. Suardiaz, D. Pascual, and M.I. Martin J. Med. Chem. 47 2004 2939
12. L. Czollner, G. Szilagyi, J. Lango, and J. Janaky Arch. Pharm. 323 1990 225
13. U.C. Yoon, S.J. Cho, Y.J. Lee, M.J. Mancheno, and P.S. Mariano J. Org. Chem. 60 1995 2353
14. M.R. Atkinson, and J.B. Polya J. Chem. Soc. 1952 3418
15. G. Pellizzari Gazz. Chim. Ital. 41 1911 93
16. CCDC-828998 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
17. W.L.F. Armarego, and C.L.L. Chai Purification of Laboratory Chemicals 6th ed. 2009 Elsevier Oxford
18. D.A. Evans, P. Nagorny, and R. Xu Org. Lett. 8 2006 5669
19. H. Nakayama, and A. Itoh Synlett 2008 675
20. P. Reynaud, E. Nguyen-Tri-Xuong, C. Davrinche, G. Tran, P. Rinjard, F. Pieri, and M.L. Arnould-Guerin Eur. J. Med. Chem. 27 1992 245
21. Y. Lin, and S.A. Lang Synthesis 1980 119
22. T. Kametani, K. Kigasawa, H. Shimizu, S. Saitou, S. Hayashida, and M. Fujino Yakugaku Zasshi 103 1983 1144
23. L. Wang, H. Fu, Y. Jinag, and Y. Zhao Chem. - Eur. J. 14 2008 10722
24. Z. Habibi, P. Salehi, M.A. Zolfigol, and M. Yousefi Synlett 2009 1506
25. Z. Habibi, P. Salehi, M.A. Zolfigol, and M. Yousefi Synlett 2007 812
26. K. Krohn, C. Franke, P.G. Jones, H.J. Aust, S. Draeger, and B. Schulz Liebigs Ann. Chem. 1992 789
27. P. Metra, and J. Hamelin Can. J. Chem. 60 1982 285
28. S.T. Staben, and N. Blaquiere Angew. Chem., Int. Ed. 49 2010 325
29. Y. Lin, J.J. Hlavka, P. Bitha, and S.A. Lang J. Heterocycl. Chem. 20 1983 1693
30. Jagerovic, N.; Goya Laza, M. P.; Hernandez Folgado, L.; Alcorta Osoro, I. J.; Martin Fontelles, M. I.; Suardiaz Garcia, M. L.; Dannert, M. T. World Patent WO03082833, 2003.
31. K.B. Jorgensen, R.B. Olsen, and P.H.J. Carlsen Molecules 6 2001 481