Synthesis of (NH)m(NMe)4-m-bridged calix[4]pyridines and the effect of NH bridge on structure and properties

Journal of Organic Chemistry

Volumn 74, Issue 22, 2009, Pages 8595-8603

  Zhang, En Xuan ^a   Wang, De Xian ^a   Huang, Zhi Tang ^a   Wang, Mei Xiang ^a,b  

^a INSTITUTE OF CHEMISTRY   (China)

^b Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL GROUPS; CHEMICAL EQUATIONS; CONFORMATIONAL STRUCTURES; CONJUGATION SYSTEM; COUPLING REACTION; DEPROTECTION; FLUORESCENCE INTENSITIES; INTERCONVERSIONS; MACROCYCLICS; PYRIDINE DERIVATIVES; SELECTIVE FLUORESCENCE; STRUCTURE AND PROPERTIES; TIME-SCALES;

CHEMICAL BONDS; CONFORMATIONS; FLUORESCENCE; FLUORINE CONTAINING POLYMERS; SYNTHESIS (CHEMICAL); ZINC; ZINC COMPOUNDS;

PYRIDINE;

CALIX[4]PYRIDINE DERIVATIVE; HETEROCYCLIC COMPOUND; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DEPROTECTION REACTION; REACTION ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS;

CYCLIZATION; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 70449629337     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901609u     Document Type: Article

References (55)

1. For useful reviews of heterocalixaromatics, see: (a) Wang, M.-X. Chem. Commun. 2008, 4541.
2. (b) Maes, W.; Dehaen, W. Chem. Soc. Rev. 2008, 37, 2393.
3. (c) Tsue, H.; Ishibashi, K.; Tamura, R. Top. Heterocycl. Chem. 2008, 17, 73.
4. (d)König, B.; Fonseca, M. H. Eur. J. Inorg. Chem. 2000, 2303.
5. For recent examples of nitrogen-bridged calixaromatics, see: (a) Ito,A.; Ono, Y.; Tanaka, K. New J.Chem. 1998, 779.
6. (b) Ito, A.;Ono,Y.; Tanaka, K. J. Org. Chem. 1999, 64, 8236.
7. (c) Miyazaki; Kanbara, T.; Yamamoto, T Tetrahedron Lett. 2002, 43, 7945.
8. (d) Wang, M.-X.; Zhang, X.-H.; Zheng, Q.-Y. Angew. Chem., Int. Ed. 2004, 43, 838.
9. (e) Gong, H.-Y.; Zhang, X.-H.; Wang, D.-X.;Ma, H.-W.; Zheng, Q.-Y.; Wang, M.-X. Chem. - Eur. J. 2006, 12, 9262.
10. (f) Gong, H.-Y.; Zheng, Q.-Y.; Zhang, X.-H.;Wang, D.-X.; Wang, M.-X. Org. Lett. 2006, 8, 4895.
11. (g) Tsue, H.; Ishibashi, K.; Takahashi, H.; Tamura, R. Org. Lett. 2005, 7, 11.
12. (h) Fukushima, W.; Kanbara, T.; Yamamoto, T. Synlett 2005, 19, 2931.
13. (i) Selby, T. D.; Blackstock, S. C. Org. Lett. 1999, 1, 2053.
14. (j) Suzuki, Y.; Yanagi, T.; Kanbara, T.; Yamamoto, T. Synlett 2005, 2, 263.
15. (k) Ishibashi, K.; Tsue, H.; Tokita, S.; Matsui, K.; Takahashi, H.; Tamura, R. Org. Lett. 2006, 8, 5991.
16. (l) Gong, H.-Y.; Wang, D.-X.; Xiang, J.-F.; Zheng, Q.-Y.; Wang, M.-X. Chem.;Eur. J. 2007, 13, 7791.
17. (m) Liu, S.-Q.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Chem. Commun. 2007, 3856.
18. (n) Zhang, E.-X.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Org. Lett. 2008, 10, 2565.
19. (o)Gong, H.-Y.;Wang,D.-X.; Zheng,Q.-Y.; Wang, M.-X. Tetrahedron 2009, 65, 87.
20. For recent examples of oxygen-bridged calixaromatics, see: (a)Wang, M.-X.; Yang, H.-B. J. Am. Chem. Soc. 2004, 126, 15412.
21. (b) Katz, J. L.; Feldman, M. B.; Conry, R. R. Org. Lett. 2005, 7, 91.
22. (c) Katz, J. L.; Selby, K. J.; Conry,R.R. Org. Lett. 2005, 7, 3505.
23. (d)Katz, J.L.; Geller,B. J.; Conry,R. R. Org. Lett. 2006, 8, 2755.
24. (e) Maes, W.; Van Rossom, W.; Van Hecke, K.; VanMeervelt, L.; Dehaen, W. Org. Lett. 2006, 8, 4161.
25. (f) Hao, E.; Fronczek, F. R.; Vicente, M. G. H. J. Org. Chem. 2006, 71, 1233.
26. (g) Chambers, R. D.; Hoskin, P. R.; Kenwright, A. R.; Khalil, A.; Richmond, P.; Sandford, G.; Yufit, D. S.; Howard, J. A. K. Org. Biomol. Chem. 2003, 2137.
27. (h) Chambers, R. D.; Hoskin, P. R.; Khalil, A.; Richmond, P.; Sandford, G.; Yufit, D. S.; Howard, J. A. K. J. Fluorine Chem. 2002, 116, 19.
28. (i) Li, X. H.; Upton, T. G.; Gibb,C.L.D.; Gibb,B.C. J.Am. Chem. Soc. 2003, 125, 650.
29. (j)Yang,F.;Yan, L.-W.; Ma, K.-Y.; Yang, L.; Li, J.-H.; Chen, L.-J.; You, J.-S. Eur. J. Org. Chem. 2006, 1109.
30. (k)Wang, Q.-Q.;Wang,D.-X.;Zheng,Q.-Y.;Wang,M.-X. Org. Lett. 2007, 9, 2847.
31. (l) Katz, J. L.; Geller, B. J.; Foster, P. D. Chem. Commun. 2007, 1026.
32. (m) Zhang,C.; Chen,C.-F. J. Org. Chem. 2007, 72, 3880.
33. (n) Van Rossom, W.; Maes, W.; Kishore, L.; Ovaere, M.; Van Meervelt, L.; Dehaen, W. Org. Lett. 2008, 10, 585.
34. For review on thiacalixarenes, see: Morohashi, N.; Narumi, F.; Iki, N.; Hattori, T.; Miyano, S. Chem. Rev. 2006, 106, 5291.
35. For examples of other heteroatom-bridged calixaromatics, see: (a) König, B.; Rödel, M.; Bubenitschek, P.; Jones, P. G.; Thondorf, I. J. Org. Chem. 1995, 60, 7406.
36. (b) König, B.; Rödel, M.; Bubenitschek, P.; Jones, P. G. Angew. Chem., Int. Ed. 1995, 34, 661.
37. (c) Yoshida, M.; Goto, M.; Nakanishi, F. Organometallics 1999, 18, 1465.
38. (d) Avarvari, N.; Mezailles, N.; Ricard, L.; Le Floch, P.; Mathey, F. Science 1998, 280, 1587.
39. (e) Avarvari, N.; Maigrot, N.; Ricard, L.; Mathey, F.; Le Floch, P. Chem.; Eur. J. 1999, 5, 2109.
40. Wang, D.-X.; Zheng, Q.-Y.; Wang, Q.-Q.; Wang, M.-X. Angew. Chem., Int. Ed. 2008, 47, 7485.
41. (a) Yang, H.-B.; Wang, D.-X.; Wang, Q.-Q.; Wang, M.-X. J. Org. Chem. 2007, 72, 3757.
42. (b) Hou, B.-Y.; Wang, D.-X.; Yang, H.-B.; Zheng, Q.-Y.; Wang, M.-X. J. Org. Chem. 2007, 72, 5218.
43. (c) Hou, B.-Y.; Zheng, Q.-Y.; Wang, D.-X.; Wang, M.-X. Tetrahedron 2007, 63, 10801.
44. (d) Hou, B.-Y.; Zheng, Q.-Y.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Chem. Commun. 2008, 3864.
45. (e) Yao, B.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Chem. Commun. 2009, 2899.
46. The N-arylation of NH-bridged calix[2]arene[2]triazine was reported: Wang, Q.-Q.;Wang,D.-X.;Ma,H.-W.;Wang,M.-X. Org. Lett. 2006, 8, 5967.
47. Touil, M.; Lachkar, M.; Siri, O. Tetrahedron Lett. 2008, 49, 7250.
48. Konishi,H.;Hashimoto, S.; Sakakibara,T.;Matsubara, S.;Yasukawa, Y.; Morikawa, O.; Kobayashi, K. Tetrahedron Lett. 2009, 50, 620.
49. (a) Vale, M.; Pink, M.; Rajca, S.; Rajca, A. J. Org. Chem. 2008, 73, 27.
50. (b) Tsue, H.; Ishibashi, K.; Tokita, S.; Takahashi, H.; Matsui, K.; Tamura, R. Chem.;Eur. J. 2008, 14, 6125.
51. (c) Tsue, H.; Matsui, K.; Ishibashi, K.; Takahashi, H.; Tokita, S.; Ono, K.; Tamura, R. J. Org. Chem. 2008, 73, 7748.
52. Yao, B.; Wang, D.-X.; Gong, H.-Y.; Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 2009, 74, 5361.
53. Gigg, R.; Conant, R. J. Carbohydr. Chem. 1983, 1, 331.
54. (a) Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739.
55. (b)Hyperquad2003 software, Protonic Software, http://www.hyperquad.co.uk