Citation: Zai-Gang Luo, Yu Zhao, Feng Xu, Chao Ma, Xue-Mei Xu, Xiao-Mei Zhang. Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K₂CO₃-catalyzed 1,3-dipolar cycloaddition reaction[J]. Chinese Chemical Letters, ;2014, 25(10): 1346-1348. doi: 10.1016/j.cclet.2014.05.013 shu

Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K₂CO₃-catalyzed 1,3-dipolar cycloaddition reaction

1.
College of Chemical Engineering, Anhui University of Science & Technology, Huainan 232001, China

Corresponding author: Zai-Gang Luo, Xue-Mei Xu,
Received Date: 11 March 2014
Available Online: 4 May 2014
Fund Project: The authors gratefully thank the financial supports of the National Natural Science Foundation of China (No. 21102003) (No. 21102003)

Two calix[4]arene derivatives containing 1,2,3-triazole moiety were synthesized via K₂CO₃-catalyzed 1,3-dipolar cycloaddition reaction between calix[4]arene-based azide and active methylene compounds in good yields. The structures of the two compounds synthesized herein were fully confirmed by ¹H NMR, ¹³C NMR, and MS (ESI). The thermal analysis showed that the mass losses of the synthesized compounds 4 and 5 containing 1,2,3-triazole groups are similar to each other.
- Calix[4]arene derivative,
- 1,2,3-Triazole,
- 1,3-Dipolar cycloaddition,
- Synthesis
1. [1]
  [1] X.M. Chen, Z.J. Li, Z.X. Ren, Z.T. Huang, Synthesis of glucosylated 1,2,3-triazole derivatives, Carbohydr. Res. 315 (1999) 262-267.
2. [2]
  [2] L.L. Brockunier, E.R. Parmee, H.O. Ok, et al., Human beta3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides, Bioorg. Med. Chem. Lett. 10 (2000) 2111-2114.
3. [3]
  [3] M.J. Genin, D.A. Allwine, D.J. Anderson, et al., Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenza and Moraxella catarrhalis, J. Med. Chem. 43 (2000) 953-970.
4. [4]
  [4] R. Alvarez, S. Velazquez, A. San-Felix, et al., 1,2,3-Triazole-20,50-bis-O-(tert-butyl-dimethylsilyl)-b-D-ribofuranosyll-3'-spiro-5"-(4'-amino-l",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity, J. Med. Chem. 37 (1994) 4185-4194.
5. [5]
  [5] S. Velazquez, R. Alvarez, C. Perez, et al., Regiospecific synthesis and anti-human immuno-deficiency virus activity of novel 5-substituted N-alkylcarbamoyl and N, N-dialkyl carbamoyl 1,2,3-triazole-TSAO analogues, J. Antiviral Chem. Chemother. 9 (1998) 481-489.
6. [6]
  [6] R. Huisgen, in: A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry, vol. 1, Wiley, New York, 1984, pp. 1-176.
7. [7]
  [7] F. Xie, K. Sivakumar, Q. Zeng, et al., A fluorogenic ‘click' reaction of azidoanthracene derivatives, Tetrahedron 64 (2008) 2906-2914.
8. [8]
  [8] K. Sivakumar, F. Xie, B. Cash, et al., A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes, Org. Lett. 6 (2004) 4603-4606.
9. [9]
  [9] V.R. Kamalraj, S. Senthil, P. Kannan, One-pot synthesis and the fluorescent behavior of 4-acetyl-5-methyl-1,2,3-triazole regioisomers, J. Mol. Struct. 892 (2008) 210-215.
10. [10]
  [10] I.F. Cottrell, D. Hands, P.G. Houghton, G.R. Humphrey, S.H.B. Wright, An improved procedure for the preparation of 1-benzyl-1H-1,2,3-triazoles form benzyl azides, J. Heterocycl. Chem. 28 (1991) 301-304.
11. [11]
  [11] (a) Y. Liu, C. You, H. Zhang, Supramolecular Chemistry-Molecular Recognition and Assembly of Synthetic Receptors, Nankai University Press, 2001;
12. [12]
  (b) L. Mandolini, R. Ungaro, Calixarenes in Action, Imperial College Press, London, 2000;
13. [13]
  (c) Z. Asfari, W. Bohmer, J. Harrowfield, et al., Calixarenes, Kluwer Academic Press, Dordrecht, 2001.
14. [14]
  [12] (a) A. Vecchi, B. Melai, A. Marra, C. Chiappe, A. Dondoni, Microwave-enhanced ionothermal CuAAC for the synthesis of glycoclusters on a calix[4]arene platform, J. Org. Chem. 73 (2008) 6437-6440;
15. [15]
  (b) S.Y. Park, J.H. Yoon, C.S. Hong, et al., A pyrenyl-appended triazole-based calix[4]arene as a fluorescent sensor for Cd²⁺ and Zn²⁺, J. Org. Chem. 73 (2008) 8212-8218;
16. [16]
  (c) B.T. Zhao, X.M. Zhu, X.H. Chen, Z.N. Yan, W.M. Zhu, Novel clicked tetrathiafulvalene-calix[4]arene assemblies: synthesis and intermolecular electron transfer toward p-chloranil, Chin. Chem. Lett. 24 (2013) 573-577;
17. [17]
  (d) H. Chen, Z.L. Zou, S.L. Tan, et al., Efficient synthesis of water-soluble calix[4]-arenes via thiol-ene "click" chemistry, Chin. Chem. Lett. 24 (2013) 367-369.
18. [18]
  [13] C.D. Gutsche, M. Iqbal, D. Stewart, Calixarenes. 19. Syntheses procedures for ptertbutylcalix[4]arene, J. Org. Chem. 51 (1986) 742-745.
19. [19]
  [14] Z.T. Li, G.Z. Ji, C.X. Zhao, et al., Self-assembling calix[4]arene catenanes preorganization, conformation, selectivity, and efficiency, J. Org. Chem. 64 (1999) 572-3584.
20. [20]
  [15] F. Szemes, D. Hesek, Z. Chen, et al., Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(Ⅱ) bipyridyl receptor molecules that recognize and sense anions, Inorg. Chem. 35 (1996) 5868-5879.
21. [21]
  [16] V.S. Talanov, R.A. Bartsch, Highly selective preparation of conformationally rigidstereoisomeric calix[4]arenes with two carboxymethoxy groups, J. Chem. Soc., Perkin Trans. 1 (1999) 1957-1961.
22. [22]
  [17] C. Jaime, J. de Mendoza, P. Prados, P. Nieto, C. Sanchez, Carbon-13 NMR chemical shifts. A single rule to determine the conformation of calix[4]arenas, J. Org. Chem. 56 (1991) 3372-3376.
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Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K2CO3-catalyzed 1,3-dipolar cycloaddition reaction

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通讯作者: 陈斌, bchen63@163.com

Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K₂CO₃-catalyzed 1,3-dipolar cycloaddition reaction