Calix[2]triazole[2]arenes; A class of hybrid heterocalixarenes

European Journal of Organic Chemistry

Volumn , Issue 21, 2013, Pages 4614-4623

  Cho, Jihee ^a   Lee, Seokwoo ^a   Hwang, Soonho ^a   Kim, Sang Hoon ^b   Kim, Jong Seung ^b   Kim, Sanghee ^a  

^a Seoul National University   (South Korea)

^b Korea University   (South Korea)

Author keywords

Calixarenes; Click chemistry; Conformation analysis; Structure elucidation; Supramolecular chemistry

Indexed keywords

EID: 84880044555     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300401     Document Type: Article

References (56)

1. Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, Calixarenes 2001, Kluwer, Dordrecht, The Netherlands, 2001.
2. V. Böhmer, in: The Chemistry of Phenols (Ed.:, Z. Rappoport), Wiley, Chichester, 2003, chapter 19.
3. J. Vicens, J. Harrowfield, Calixarenes, in: the Nanoworld, Springer, Dordrecht, The Netherlands, 2007.
4. L. Mandolini, R. Ungaro, Calixarenes in Action, Imperial College Press, London, 2000.
5. J. S. Kim, D. T. Quang, Chem. Rev. 2007, 107, 3780-3799.
6. S. Kumar, D. Paul, H. Singh, in: Advances in Heterocyclic Chemistry, vol. 89 (Ed.:, A. R. Katritzky), Elsevier, Amsterdam, 2005, p. 65.
7. W. Sliwa, Chem. Heterocycl. Compd. 2004, 40, 683-700.
8. D. T. Quang, J. S. Kim, Chem. Rev. 2010, 110, 6280-6301.
9. R. K. Pathak, K. Tabbasum, A. Rai, D. Panda, C. P. Rao, Analyst 2012, 137, 4069-4075.
10. R. K. Pathak, V. K. Hinge, K. Mahesh, A. Rai, D. Panda, C. P. Rao, Anal. Chem. 2012, 84, 6907-6913.
11. R. K. Pathak, V. K. Hinge, A. Rai, D. Panda, C. P. Rao, Inorg. Chem. 2012, 51, 4994-5005.
12. S. C. Picot, B. R. Mullaney, P. D. Beer, Chem. Eur. J. 2012, 18, 6230-6237.
13. R. K. Pathak, J. Dessingou, C. P. Rao, Anal. Chem. 2012, 84, 8294-8300.
14. R. K. Pathak, V. K. Hinge, P. Mondal, C. P. Rao, Dalton Trans. 2012, 41, 10652-10660.
15. V. V. S. Mummidivarapu, A. Nehra, V. K. Hinge, C. P. Rao, Org. Lett. 2012, 14, 2968-2971.
16. Y. Hua, R. O. Ramabhadran, E. O. Uduehi, J. A. Karty, K. Raghavachari, A. H. Flood, Chem. Eur. J. 2011, 17, 312-321.
17. J. L. Sessler, J. Cai, H.-Y. Gong, X. Yang, J. F. Arambula, B. P. Hay, J. Am. Chem. Soc. 2010, 132, 14058-14060.
18. Y. Hua, A. H. Flood, Chem. Soc. Rev. 2010, 39, 1262-1271.
19. M. Juríček, P. H. J. Kouwer, A. E. Rowan, Chem. Commun. 2011, 47, 8740-8749.
20. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
21. Y. Bourne, H. C. Kolb, Z. Radic̈, K. B. Sharpless, P. Taylor, P. Marchot, Proc. Natl. Acad. Sci. USA 2004, 101, 1449-1454.
22. N. Kovačevic̈, A. Kokalj, J. Phys. Chem. C 2011, 115, 24189-24197.
23. N. G. Angelo, P. S. Arora, J. Am. Chem. Soc. 2005, 127, 17134-17135.
24. N. K. Andersen, H. Døssing, F. Jensen, B. Vester, P. Nielsen, J. Org. Chem. 2011, 76, 6177-6187.
25. A. Trabocchi, G. Menchi, N. Cini, F. Bianchini, S. Raspanti, A. Bottoncetti, A. Pupi, L. Calorini, A. Guarna, J. Med. Chem. 2010, 53, 7119-7128.
26. Y. Wu, Y. Dong, J. Li, X. Huang, Y. Cheng, C. Zhu, Chem. Asian J. 2011, 6, 2725-2729.
27. E. Hrishikesan, C. Saravanan, P. Kannan, Ind. Eng. Chem. Res. 2011, 50, 8225-8229.
28. E. V. Dzyuba, L. Kaufmann, N. L. Löw, A. K. Meyer, H. D. F. Winkler, K. Rissanen, C. A. Schalley, Org. Lett. 2011, 13, 4838-4841.
29. M.-H. Ryu, J.-W. Choi, H.-J. Kim, N. Park, B.-K. Cho, Angew. Chem. 2011, 123, 5855-5858; .
30. Angew. Chem. Int. Ed. 2011, 50, 5737-5740
31. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711; .
32. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
33. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
34. M. Caricato, A. Olmo, C. Gargiulli, G. Gattuso, D. Pasini, Tetrahedron 2012, 68, 7861-7866.
35. J. Hu, J. Wu, J. Lu, Y. Ju, Tetrahedron Lett. 2012, 53, 6705-6709.
36. A. Noor, J. E. M. Lewis, S. A. Cameron, S. C. Moratti, J. D. Crowley, Supramol. Chem. 2012, 24, 492-498.
37. R. K. Chhatra, A. Kumar, P. S. Pandey, J. Org. Chem. 2011, 76, 9086-9089.
38. M. L. Conte, D. Grotto, A. Chambery, A. Dondoni, A. Marra, Chem. Commun. 2011, 47, 1240-1242.
39. V. Haridas, S. Sahu, P. Venugopalan, Tetrahedron 2011, 67, 727-733.
40. R. Rajesh, G. Periyasami, R. Raghunathan, Tetrahedron Lett. 2010, 51, 1896-1898.
41. For a review on the synthesis of calixarenes by stepwise methods, see:, V. Böhmer, Liebigs Ann./Recueil 1997, 2019-2030.
42. K. Tsubaki, K. Mukoyoshi, T. Otsubo, K. Fuji, Chem. Pharm. Bull. 2000, 48, 882-884.
43. C. H. Larsen, K. W. Anderson, R. E. Tundel, S. L. Buchwald, Synlett 2006, 2941-2946.
44. A. Orsini, A. Vitérisi, A. Bodlenner, J.-M. Weibel, P. Pale, Tetrahedron Lett. 2005, 46, 2259-2262.
45. A. Carpita, L. Mannocci, R. Rossi, Eur. J. Org. Chem. 2005, 1859-1864.
46. R. J. Kurland, M. B. Rubin, W. B. Wise, J. Chem. Phys. 1964, 40, 2426-2427.
47. I. Thondorf, A. Shivanyuk, V. Böhmer, in: Calixarenes 2001 (Eds.:, M.-Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer, Dordrecht, The Netherlands, 2001, p. 27.
48. A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734.
49. S. G. Smith, J. M. Goodman, J. Am. Chem. Soc. 2010, 132, 12946-12959.
50. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
51. R. Ditchfield, J. Chem. Phys. 1972, 56, 5688-5691.
52. K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
53. C. Adamo, V. Barone, J. Chem. Phys. 1998, 108, 664-675.
54. W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
55. S. Simaan, S. E. Biali, J. Org. Chem. 2003, 68, 7685-7692.
56. C. D. Gutsche, in: Calixarenes Revisited, Royal Society of Chemistry, Cambridge, 1998, p. 63.