Citation: Xue-Zhi Cheng, Wei Liu, Zhen-Dong Huang, Chun-Xiang Kuang. Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides[J]. Chinese Chemical Letters, ;2013, 24(8): 764-766. shu

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

1.
a Department of Chemistry, Tongji University, Shanghai 200092, China;
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b Zhejiang Citrus Research Institute, Taizhou 318020, China;
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c Key Laboratory of Yangtze River Water Environment, Ministry of Education, Shanghai 200092, China

Corresponding author: Chun-Xiang Kuang,
Received Date: 28 March 2013
Available Online: 27 April 2013

A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields.
- Cyclizations,
- Heterocycles,
- Sodium hydride,
- Triazoles
1. [1]
  [1] R. Moumne, V. Larue, B. Seijo, et al., Tether influence on the binding properties of tRNA₃^Lys ligands designed by a fragment-based approach, Org. Biomol. Chem. 8 (2010) 1154-1159.
2. [2]
  [2] G.K. Rawal, P. Zhang, C. Ling, Controlled synthesis of linear α-cyclodextrin oligomers using copper-catalyzed Huisgen 1,3-dipolar cycloaddition, Org. Lett. 12 (2010) 3096-3099.
3. [3]
  [3] M.P. Ahsanullah, P. Schmieder, R. Kuhne, J. Rademann, Metal-free, regioselective triazole ligations that deliver locked cis peptide mimetics, Angew. Chem. Int. Ed. 48 (2009) 5042-5045.
4. [4]
  [4] H. Duan, S. Sengupta, J.L. Petersen, N.G. Akhmedov, X. Shi, Triazole-Au
5. [5]
  (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.
6. [6]
  [5] C.W. Tornøe, C. Christensen, M. Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper
7. [7]
  (i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides, J. Org. Chem. 67 (2002) 3057-3064.
8. [8]
  [6] G. Labbe, P. Ykman, G. Smets, Reactions of azides with a-ester phosphorus ylids, Tetrahedron 25 (1969) 5421-5426.
9. [9]
  [7] S. Fioravanti, L. Pellacani, D. Ricci, P.A. Tardella, Stereoselective azide cycloaddition to chiral cyclopentanone enamines, Tetrahedron: Asymmetry 8 (1997) 2261.
10. [10]
  [8] A. Krasinski, V.V. Fokin, K.B. Sharpless, Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited, Org. Lett. 6 (2004) 1237-1240.
11. [11]
  [9] S.W. Kwok, J.R. Fotsing, R.J. Fraser, V.O. Rodionov, V.V. Fokin, Transition-metalfree catalytic synthesis of 1,5-diaryl-1,2,3-triazoles, Org. Lett. 12 (2010) 4217-4219.
12. [12]
  [10] B.C. Boren, S. Narayan, L.K. Rasmussen, et al., Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism, J. Am. Chem. Soc. 130 (2008) 8923-8930.
13. [13]
  [11] M. Zhao, C. Kuang, X.Z. Cheng, Q. Yang, Iron-catalyzed ketonization of 2-aryl-1,1-dibromoalkenes with KOAc: synthesis of a-acetoxy aryl ketones via a Michaellike addition process, Chin. Chem. Lett. 22 (2011) 571-574.
14. [14]
  [12] S. Brase, C. Gil, K. Knepper, V. Zimmermann, Organic azides: an exploding diversity of a unique class of compounds, Angew. Chem. Int. Ed. 44 (2005) 5188-5240.
15. [15]
  [13] X.Z. Cheng, Y. Yang, C. Kuang, Q. Yang, Copper
16. [16]
  (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.
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沈阳化工大学材料科学与工程学院沈阳 110142