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

  • 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.
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    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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