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Syntheses, reactions and crystal structures of 1,3-alternate p-tert-butylthiacalix[4]arene esters and amides

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Abstract

p-tert-Butylthiacalix[4]arene was efficiently alkylated in the system of K2CO3/KI/acetone to give several thiacalixarene derivatives in 1,3-alternate conformation with functional ester, chloro, cyano and amide groups. Thiacalixarene tetraacateate can be converted to bicyclic amides by ammonolysis with alkylenediamine, and to sulfonylcalixarene by oxidation with hydrogen peroxide in acetic acid. Single crystal X-ray diffraction analysis reveals that thiacalixarene and sulfonylcalixarene exist mainly in 1,3-alternate conformation.

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Syntheses, reactions and crystal structures of p-tert-Butylthiacalix[4]arene esters and amides

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References

  1. Lhoták, P.: Chemistry of thiacalixarenes. Eur. J. Org. Chem. 1671–1692 (2004)

  2. Morohashi, N., Narumi Iki, N., Hattori, T., Miyano, S.: Thiacalixarenes. Chem. Rev. 106, 5291–5316 (2006)

    Article  CAS  Google Scholar 

  3. Liu, L., Han, J., Yan, C.G.: Progress in study of novel supramolecular host-thiacalixarene. Chin. J. Org. Chem. 27, 907–917 (2007)

    CAS  Google Scholar 

  4. Iki, N., Miyano, S.: Can thiacalixarene surpass calixarene. J. Incl. Phenom. Macrocycl. Chem. 41, 99–105 (2001)

    Article  CAS  Google Scholar 

  5. Dhir, A., Bhalla, V., Kumar, M.: Ratiometry of monomer/excimer emissions of dipyrenyl thiacalix[4]arene for Cu2+ detection: a potential Cu2+ and K+ switched INHIBIT logic gate with NOT and YES logic functions. Tetrahedron Lett. 49, 4227–4230 (2008)

    Article  CAS  Google Scholar 

  6. Stoikov, I.I., Yushkova, E.A., Zhukov, A.Y., Zharov, H., Antipin, I.S., Konovalov, A.I.: The synthesis of p-tert-butyl thiacalix[4]arenes functionalized with secondary amide groups at the lower rim and their extraction properties and self-assembly into nanoscale aggregates. Tetrahedron 64, 7112–7121 (2008)

    Article  CAS  Google Scholar 

  7. Li, X., Gong, S.L., Yang, W.P., Chen, Y.Y., Meng, X.G.: The influence of isomerism on the self-assembly behavior and complexation property of 1,3-alternate tetraaminopyridyl-thiacalix[4]arene derivatives. Tetrahedron 64, 6230–6237 (2008)

    Article  CAS  Google Scholar 

  8. Šimánová, M., Dvořáková, H., Stibor, I., Pojarová, M., Lhoták, P.: Synthesis and conformational behaviour of lower-rim tetraacetylated thiacalix[4]arenes. Tetrahedron Lett. 49, 1026–1029 (2008)

    Article  Google Scholar 

  9. Štastný, V., Stibor, I., Dvořáková, H., Lhoták, P.: Synthesis of (thia)calix[4]arene oligomers: towards calixarene-based dendrimers. Tetrahedron 60, 3383–3391 (2004)

    Article  Google Scholar 

  10. Lhoták, P., Himl, M., Stibor, I., Petříčková, H.: Alkylation of thiacalix[4]arenes. Tetrahedron Lett. 43, 9621–9624 (2002)

    Article  Google Scholar 

  11. Desroches, C., Kessler, V., Parola, S.: The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes. Tetrahedron Lett. 45, 6329–6331 (2004)

    Article  CAS  Google Scholar 

  12. Duta, M., Asfri, Z., Kruchinina, N., Thurey, P., Hagege, A., Leroy, M.: Thiacrowncalix[4]arene derivatives: synthesis and complexing properties. Supramol. Chem. 17, 221–226 (2005)

    Article  CAS  Google Scholar 

  13. Bhalla, V., Kumar, M., Hattori, M.S.: Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene. Tetrahedron 60, 5881–5887 (2004)

    Article  CAS  Google Scholar 

  14. van Leeuwen, F.W.B., Beijleveld, H., Kooijman, H., Spek, A.L., Verboom, W., Reihoudt, D.N.: Synthesis and conformational evuation of p-tert-butylthiacalix[4]arene-crowns. J. Org. Chem. 69, 3928–3936 (2004)

    Article  Google Scholar 

  15. Iki, N., Narumi, F., Fujimoto, T., Morohashi, N., Miyano, S.: Selective synthesis of three conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]thiacalix[4]arene and their complexation properties towards alkali metal ions. J. Chem. Soc. Perkin Trans. 2, 2745–2750 (1998)

    Google Scholar 

  16. Singh, S.P., Chakrabarti, A., Chawla, H.M., Pant, N.: Aminolysis of p-tert-butyltetrathiacalix[4]arene tetraethylacetates in cone, partial cone and 1, 3-alternate conformation: synthesis of amide based receptors for oxyanions. Tetrahedron 64, 1983–1987 (2008)

    Article  CAS  Google Scholar 

  17. Akdas, H., Mislin, G., Graf, E., Hosseini, M.W., Cian, A.D., Fischer, J.: Synthesis and solid state structural analysis of conformers of tetrakis((ethoxycarbonyl)methoxy)tetrathiacalix[4]arene. Tetrahedron Lett. 40, 2113–2116 (1999)

    Article  CAS  Google Scholar 

  18. Št’astný, V., Stibor, I., Petrickova, H., Sýkora, J., Lhoták, P.H.: Thiacalix[4]arene derivatives with proximally bridged lower rim. Tetrahedron 61, 9990–9995 (2005)

    Article  Google Scholar 

  19. Lhoták, P.: Regioselective and stereoselective oxidation of thiacalix[4]arene tetraacetate: synthesis of all possible sulfinylcalix[4]arenes. Tetrahedron 57, 4775–4779 (2001)

    Article  Google Scholar 

  20. Mislin, G., Graf, E., Hosseini, M.W., Cian, A.D., Fischer, J.: Sulfone-calixarenes: a new class of molecular building block, Chem. Commun. 134, 5–1346 (1998)

    Google Scholar 

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant No. 20672091)

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  1. College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

    Li Liu, Kun Huang & Chao Guo Yan

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  1. Li Liu
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  2. Kun Huang
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Correspondence to Chao Guo Yan.

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Liu, L., Huang, K. & Yan, C.G. Syntheses, reactions and crystal structures of 1,3-alternate p-tert-butylthiacalix[4]arene esters and amides. J Incl Phenom Macrocycl Chem 66, 349–355 (2010). https://doi.org/10.1007/s10847-009-9652-4

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