Hydrogen-bonding-induced planar, rigid, and zigzag oligoanthranilamides. Synthesis, characterization, and self-assembly of a metallocyclophane

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6221-6227

  Zhu, Jiang ^a   Wang, Xiao Zhong ^b   Chen, Ying Qi ^b   Jiang, Xi Kui ^a   Chen, Xin Zhi ^b   Li, Zhan Ting ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; HYDROGEN BONDS; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE; RIGIDITY; SELF ASSEMBLY; SOLUTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

HYDROGEN-BONDING-INDUCED PLANAR; METALLOCYCLOPHANE; OLIGOAMIDES; SUBMOLECULAR ARCHITECTURE;

OLIGOMERS;

BENZAMIDE DERIVATIVE; OLIGOANTHRANILAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 4644337027     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0490705     Document Type: Article

References (61)

1. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
2. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
3. (c) Stigers, K. D.; Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1999, 3, 714.
4. (d) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
5. (e) Sanford, A. R.; Gong, B. Curr. Org. Chem. 2003, 7, 1649.
6. (f) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
7. (g) Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650.
8. (h) Patch, J. A.; Barron, A. E. Curr. Opin. Chem. Biol. 2002, 6, 872.
9. (i) Schmuck, C. Angew. Chem., Int. Ed. 2003, 42, 2448.
10. (j) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807.
11. (k) Huc, I. Eur. J. Org. Chem. 2004, 17.
12. Cuccia, L. A.; Lehn, J.-M.; Homo, J.-C.; Schmutz, M. Angew. Chem., Int. Ed. 2000, 39, 233.
13. (a) Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303.
14. (b) Zych, A. J.; Iverson, B. L. Helv. Chim. Acta 2002, 85, 3294.
15. (c) Zhao, X.; Jia, M.-X.; Jiang, X.-K.; Wu, L.-Z.; Li, Z.-T.; Chen, G.-Z. J. Org. Chem. 2004, 69, 270.
16. (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793.
17. (b) Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120.
18. (a) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587.
19. (b) Ernst, J. T.; Becerril, J.; Park, H. S.; Yin, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2003, 42, 535.
20. (c) Gong, B. Chem.-Eur. J. 2001, 7, 4337.
21. (d) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4352.
22. (e) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
23. For recent examples of other intramolecular H-bond-stabilized oligoamide strands, see: (a) Armand, P.; Kirshenbaum, K.; Goldsmith, R. A.; Farr-Jones, S.; Barron, A. E.; Truong, K. T.; Dill, K. A.; Mierke, D. F.; Cohen, F. E.; Zuckermann, R. N.; Bradley, E. K. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4309.
24. (b) Corbin, P. S.; Zimmerman, S. C.; Thiessen, P. A.; Hawryluk, N. A.; Murray, T. J. J. Am. Chem. Soc. 2001, 123, 10475.
25. (c) Winkler, J. D.; Piatnitski, E. L.; Mehlmann, J.; Kasparec, J.; Axelsen, P. H. Angew. Chem., Int. Ed. 2001, 40, 743.
26. (d) Nowick, J. S.; Lam, K. S.; Khasanova, T. V.; Kemnitzer, W. E.; Maitra, S.; Mee, H. T.; Liu, R. J. Am. Chem. Soc. 2002, 124, 4972.
27. (e) Hemmerlin, C.; Marraud, M.; Rognan, D.; Graff, R.; Semeteyl, V.; Briand, J.-P.; Guichard, G. Helv. Chim. Acta 2002, 85, 3692.
28. (f) Park, J. S.; Lee, H. S.; Lai, J. R.; Kim, B. M.; Gellman, S. H. J. Am. Chem. Soc. 2003, 125, 8539.
29. (g) Gademann, K.; Hane, A.; Rueping, M.; Jaun, B.; Seebach, D. Angew. Chem., Int. Ed. 2003, 42, 1534.
30. (h) Yang, D.; Li, W.; Qu, J.; Luo, S.-W.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 13018.
31. (i) Huang, B.; Prantil, M. A.; Gustafson, T. L.; Parquette, J. R. J. Am. Chem. Soc. 2003, 125, 14518.
32. (j) van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Commun. 2004, 60.
33. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529.
34. Delnoye, D. A. P.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 1996, 118, 8717.
35. Wu, Z.-Q.; Jiang, X.-K.; Zhu, S.-Z.; Li, Z.-T. Org. Lett. 2004, 6, 229.
36. For three-center hydrogen bonding in folding oligoamides, see: (a) Dolain, C.; Maurizot, V.; Huc, I. Angew. Chem., Int. Ed. 2003, 42, 2738.
37. (b) Kolomiets, E.; Berl, V.; Odriozola, I.; Stadler, A.-M.; Kyritsakas, N.; Lehn, J.-M. Chem. Commun. 2003, 2868.
38. (c) Maurizot, V.; Linti, G.; Huc, I. Chem. Commun. 2004, 924.
39. (d) Recker, J.; Tomcik, D.; Parquette, J. R. J. Am. Chem. Soc. 2000, 122, 10298.
40. (e) Huang, B.; Parquette, J. R. J. Am. Chem. Soc. 2001, 123, 2689.
41. (f) Huang, B.; Prantil, M. A.; Gustafson, T. L.; Parquette, J. R. J. Am. Chem. Soc. 2003, 125, 14518.
42. Zigzagged o-phenylene ethynylene eligomers have been described; see: (a) Jones, T. V.; Blatchly, R. A.; Tew, G. N. Org. Lett. 2003, 5, 3297.
43. For examples of duality between linear and folding tapes and rosettes, see: (a) Odriozola, I.; Kyritsakas, N.; Lehn, J.-M. Chem. Commun. 2004, 62.
44. (b) Zerkowski, J. A.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 4298.
45. (a) Kesseler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
46. (b) Liskamp, R. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 633.
47. (a) Legon, A. C. Chem. Soc. Rev. 1990, 19, 197.
48. (b) Nowick, J. S.; Powell, N. A.; Martinez, E. J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763.
49. (c) Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054.
50. (a) Blanco, M.-J.; Jimynez, M. C.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
51. (b) Baxter, P. N. W.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 102.
52. (c) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509.
53. (d) Seidel, S. R.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972.
54. (e) Schalley, C. A.; Lützen, A.; Albrecht, M. Chem.-Eur. J. 2004, 10, 1072.
55. (a) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948.
56. (b) Jiang, H.; Hu, A.; Lin, W. Chem. Commun. 2003, 96.
57. Corbett, J. F. J. Chem. Soc., Perkin Trans. 2 1972, 999.
58. Aitken, R. A.; Burns, G.; Morrison, J. J. J. Chem. Soc., Perkin Trans. 1 1998, 3937.
59. Wagner, P. J.; Meador, M. A.; Park, B.-S. J. Am. Chem. Soc. 1990, 112, 5199.
60. Naito, T.; Kuroda, E.; Miyata, O.; Ninomiya, I. Chem. Pharm. Bull. 1991, 39, 2216.
61. Zeng, H.; Miller, R. S.; Flowers, R. A.; Gong, B. J. Am. Chem. Soc. 2000, 122, 2635.