Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides

Chinese Chemical Letters

Volumn 24, Issue 8, 2013, Pages 764-766

  Cheng, Xue Zhi ^a   Liu, Wei ^a   Huang, Zhen Dong ^b   Kuang, Chun Xiang ^a,c  

^a TONGJI UNIVERSITY   (China)

^b Zhejiang Citrus Research Institute   (China)

^c BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Cyclizations; Heterocycles; Sodium hydride; Triazoles

Indexed keywords

EID: 84879976078     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.05.007     Document Type: Article

References (13)

1. R. Moumne, V. Larue, and B. Seijo Tether influence on the binding properties of tRN A 3 Lys ligands designed by a fragment-based approach Org. Biomol. Chem. 8 2010 1154 1159
2. G.K. Rawal, P. Zhang, and C. Ling Controlled synthesis of linear α-cyclodextrin oligomers using copper-catalyzed Huisgen 1,3-dipolar cycloaddition Org. Lett. 12 2010 3096 3099
3. M.P. Ahsanullah, P. Schmieder, R. Kuhne, and J. Rademann Metal-free, regioselective triazole ligations that deliver locked cis peptide mimetics Angew. Chem. Int. Ed. 48 2009 5042 5045
4. H. Duan, S. Sengupta, J.L. Petersen, N.G. Akhmedov, and X. Shi Triazole-Au(I) complexes: a new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination J. Am. Chem. Soc. 131 2009 12100 12102
5. C.W. Tornøe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67 2002 3057 3064
6. G. Labbe, P. Ykman, and G. Smets Reactions of azides with α-ester phosphorus ylids Tetrahedron 25 1969 5421 5426
7. S. Fioravanti, L. Pellacani, D. Ricci, and P.A. Tardella Stereoselective azide cycloaddition to chiral cyclopentanone enamines Tetrahedron: Asymmetry 8 1997 2261
8. A. Krasinski, V.V. Fokin, and K.B. Sharpless Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited Org. Lett. 6 2004 1237 1240
9. S.W. Kwok, J.R. Fotsing, R.J. Fraser, V.O. Rodionov, and V.V. Fokin Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles Org. Lett. 12 2010 4217 4219
10. B.C. Boren, S. Narayan, and L.K. Rasmussen Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism J. Am. Chem. Soc. 130 2008 8923 8930
11. M. Zhao, C. Kuang, X.Z. Cheng, and Q. Yang Iron-catalyzed ketonization of 2-aryl-1,1-dibromoalkenes with KOAc: synthesis of α-acetoxy aryl ketones via a Michael-like addition process Chin. Chem. Lett. 22 2011 571 574
12. S. Brase, C. Gil, K. Knepper, and V. Zimmermann Organic azides: an exploding diversity of a unique class of compounds Angew. Chem. Int. Ed. 44 2005 5188 5240
13. X.Z. Cheng, Y. Yang, C. Kuang, and Q. Yang Copper(I) iodide catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles from anti-3-aryl-2,3- dibromopropanoic acids and organic azides Synthesis 18 2011 2907 2912