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Synthesis and Modification of Novel Iminecalix[4]arene Derivatives

  • Nimse, Satish Balasaheb (Institute for Applied Chemistry and Department of Chemistry, Hallym University) ;
  • Kim, Jun-Bae (Institute for Applied Chemistry and Department of Chemistry, Hallym University) ;
  • Lee, Jeong-Tae (Institute for Applied Chemistry and Department of Chemistry, Hallym University) ;
  • Song, Keum-Soo (Biometrix Technology, Inc.) ;
  • Kim, Jung-Hoon (Biometrix Technology, Inc.) ;
  • Ta, Van-Thao (Institute for Applied Chemistry and Department of Chemistry, Hallym University) ;
  • Nguyen, Van-Thuan (Institute for Applied Chemistry and Department of Chemistry, Hallym University) ;
  • Kim, Tai-Sun (Institute for Applied Chemistry and Department of Chemistry, Hallym University)
  • Received : 2010.10.19
  • Accepted : 2011.01.27
  • Published : 2011.04.20

Abstract

The synthesis of novel iminecalix[4]arenes and further modification thereafter is described using a synthetic strategy. The reaction of the benzaldehyde derivatives with tetraamine functions on the calix[4]arene easily afforded the pure compounds in 92.4-95.7% yields, regardless of the effect of the substituents on the benzaldehyde derivatives. These compounds were stable under the conditions to obtain their analogue dialkylated in the narrow rim, with 83.2-89.9% yields. Characterization of the newly synthesized iminecalix[4]arene derivatives by spectroscopic methods revealed that all compounds are in the cone conformations.

Keywords

References

  1. Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1991.
  2. Lohtak, P.; Zieba, R.; Hromadka, V.; Stibor, I.; Sykora, J. Tetrahedron Lett. 2003, 44, 4519. https://doi.org/10.1016/S0040-4039(03)00994-8
  3. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. https://doi.org/10.1021/cr960385x
  4. Bohmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713. https://doi.org/10.1002/anie.199507131
  5. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
  6. Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443.
  7. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17. https://doi.org/10.1016/S0010-8545(03)00023-7
  8. Boiocchi, M.; Del Boca, L.; Gomez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507. https://doi.org/10.1021/ja045936c
  9. Gutsche, C. D.; Pagoria, P. F. J. Org. Chem. 1985, 50, 5795. https://doi.org/10.1021/jo00350a071
  10. Atwood, J. L.; Orr, G. W.; Bott, S. G.; Robinson, K. D. Angew. Chem., Int. Ed. Engl. 1993, 32, 1093. https://doi.org/10.1002/anie.199310931
  11. Makha, M.; Raston, C. L. Tetrahedron Lett. 2001, 42, 6215. https://doi.org/10.1016/S0040-4039(01)01218-7
  12. Kumar, S.; Chawla, H. M.; Varadarajan, R. Tetrahedron Lett. 2002, 43, 2495. https://doi.org/10.1016/S0040-4039(02)00325-8
  13. Miyaji, H.; Dudic, M.; Tucker, H. R.; Prokes, I.; Light, M. E.; Hursthouse, M. B.; Stibor, I.; Lhoták, P. Tetrahedron Lett. 2002, 43, 873. https://doi.org/10.1016/S0040-4039(01)02179-7
  14. Adruini, A.; Brindani, E.; Giorgi, G.; Pochini, A.; Secchi, A. Tetrahedron 2003, 59, 7587. https://doi.org/10.1016/S0040-4020(03)01126-8
  15. Tamburini, S.; Tomasin, P.; Vigato, P. A.; Casnati, A.; Domiano, L. Inorganica Chimica Acta 1997, 254, 209. https://doi.org/10.1016/S0020-1693(96)05529-6
  16. Hwang, G. T.; Kim, B. H. Tetrahedron Lett. 2000, 41, 5917. https://doi.org/10.1016/S0040-4039(00)00972-2
  17. Alemi, A. A.; Shaabani, B.; Dilmaghani, K. A.; Ganjali, S. T. Molecules 2001, 6, 417. https://doi.org/10.3390/60400417
  18. Guo, T.; Zheng, Q.; Yang, L.; Huang, Z. J. Incl. Phen. Macr. Chem. 2000, 36, 327. https://doi.org/10.1023/A:1008006600696
  19. Durmaz, M.; Alpaydin, S.; Sirit, A.; Yilmaz, M. Tetrahedron: Asymm. 2006, 17, 2322. https://doi.org/10.1016/j.tetasy.2006.08.008
  20. Liang, Z.; Liu, Z.; Gao, Y. Spectrochimica Acta Part A 2007, 68, 1231. https://doi.org/10.1016/j.saa.2007.01.026
  21. Klimentova, J.; Vojtísek, P. J. Mol. Struct. 2007, 826, 48. https://doi.org/10.1016/j.molstruc.2006.04.016
  22. Shinkai, S.; Tsubaki, T.; Sone, T.; Manabe, O. Tetrahedron Lett. 1985, 26, 3343. https://doi.org/10.1016/S0040-4039(00)98293-5
  23. Zhang, W. C.; Zheng, Y. S.; Huang, Z. T. Synth. Commun. 1997, 27, 3763. https://doi.org/10.1080/00397919708007300
  24. Kumar, S.; Kurur, N. D.; Chawla, H. M.; Varadarajan, R. Synth. Commun. 2001, 31, 775. https://doi.org/10.1081/SCC-100103269
  25. Wagenigen, A. M. A.; Snip, E.; Verboom, W.; Reinhoudt, D. N.; Boerrigter, H. Liebigs Ann/Recueil 1997, 2235.
  26. Dudic, M.; Colombo, A.; Sansone, F.; Casnati, A.; Donofrio, G.; Ungaro, R. Tetrahedron 2004, 60, 11613.
  27. Arduini, A.; McGregor, W. A.; Paganuzzi, D.; Pochini, A.; Secchi, A.; Ugozzoli, F.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1996, 839.
  28. Manabe, K.; Oyamada, H.; Sugita, K.; Kobayashi, S. J. Org. Chem. 1999, 64, 8054. https://doi.org/10.1021/jo991009q
  29. Jaime, C.; Mendoza, J. D.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372. https://doi.org/10.1021/jo00010a036
  30. Shu, C. M.; Liu, W. C.; Ku, M. C.; Tang, F. S.; Yeh, M. L.; Lin, L. G. J. Org. Chem. 1994, 59, 3730. https://doi.org/10.1021/jo00092a044

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