Synthesis of oligo(2-ethynylpyridines): Novel building blocks for supramolecular systems

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6697-6700

  Kawano, Tomikazu ^a   Kato, Takahiro ^a   Du, Chong Xu ^a   Ueda, Ikuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BROMINATION; OXIDATION; ROOM TEMPERATURE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 0037119658     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01542-3     Document Type: Article

References (21)

1. For recent reviews, see: (a) Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 2454-2458; (b) Ziessel, R. Synthesis 1999, 1839-1865; (c) Constable, E. C. Pure Appl. Chem. 1996, 68, 253-260; (d) Constable, E. C. Prog. Inorg. Chem. 1994, 42, 67-138.
2. For recent reviews, see: (a) Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 2454-2458; (b) Ziessel, R. Synthesis 1999, 1839-1865; (c) Constable, E. C. Pure Appl. Chem. 1996, 68, 253-260; (d) Constable, E. C. Prog. Inorg. Chem. 1994, 42, 67-138.
3. For recent reviews, see: (a) Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 2454-2458; (b) Ziessel, R. Synthesis 1999, 1839-1865; (c) Constable, E. C. Pure Appl. Chem. 1996, 68, 253-260; (d) Constable, E. C. Prog. Inorg. Chem. 1994, 42, 67-138.
4. For recent reviews, see: (a) Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 2454-2458; (b) Ziessel, R. Synthesis 1999, 1839-1865; (c) Constable, E. C. Pure Appl. Chem. 1996, 68, 253-260; (d) Constable, E. C. Prog. Inorg. Chem. 1994, 42, 67-138.
5. Kawano T., Kuwana J., Shinomaru T., Du C.-X., Ueda I. Chem. Lett. 2001;1230-1231.
6. Kawano T., Shinomaru T., Ueda I. Org. Lett. 4:2002;2545-2547.
7. Kawano T., Kuwana J., Du C.-X., Ueda I. Inorg. Chem. 41:2002;4078-4080.
8. For example, see: (a) Baxter, P. N. W. J. Org. Chem. 2000, 65, 1257-1272; (b) Ziessel, R.; Suffert, J.; Youinou, M.-T. J. Org. Chem. 1996, 61, 6535-6546 and references cited therein.
9. For example, see: (a) Baxter, P. N. W. J. Org. Chem. 2000, 65, 1257-1272; (b) Ziessel, R.; Suffert, J.; Youinou, M.-T. J. Org. Chem. 1996, 61, 6535-6546 and references cited therein.
10. For example, see: (a) Zaman, M. B.; Tomura, M.; Yamashita, Y. J. Org. Chem. 2001, 66, 5987-5995; (b) Okubo, J.; Shinozaki, H.; Koitabashi, T.; Yomura, R. Bull. Chem. Soc. Jpn. 1998, 71, 329-335; (c) Neenan, T. X.; Driessen, W. L.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 1996, 247, 43-49.
11. For example, see: (a) Zaman, M. B.; Tomura, M.; Yamashita, Y. J. Org. Chem. 2001, 66, 5987-5995; (b) Okubo, J.; Shinozaki, H.; Koitabashi, T.; Yomura, R. Bull. Chem. Soc. Jpn. 1998, 71, 329-335; (c) Neenan, T. X.; Driessen, W. L.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 1996, 247, 43-49.
12. For example, see: (a) Zaman, M. B.; Tomura, M.; Yamashita, Y. J. Org. Chem. 2001, 66, 5987-5995; (b) Okubo, J.; Shinozaki, H.; Koitabashi, T.; Yomura, R. Bull. Chem. Soc. Jpn. 1998, 71, 329-335; (c) Neenan, T. X.; Driessen, W. L.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 1996, 247, 43-49.
13. 2,6-Bis(2-pyridylethynyl)pyridine derivatives, which possess three pyridine rings, are still very rare. See: (a) Inouye, M.; Chiba, J.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176; (b) Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341-345; (c) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
14. 2,6-Bis(2-pyridylethynyl)pyridine derivatives, which possess three pyridine rings, are still very rare. See: (a) Inouye, M.; Chiba, J.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176; (b) Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341-345; (c) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
15. 2,6-Bis(2-pyridylethynyl)pyridine derivatives, which possess three pyridine rings, are still very rare. See: (a) Inouye, M.; Chiba, J.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170-8176; (b) Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341-345; (c) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416-12425.
16. No synthetic methods for compound 2b have been reported in the literature to date, although complexation studies by using 2b have been reported. See: (a) Newkome, G. R.; Onishi, M. J. Organomet. Chem. 1980, 198, 225-229; (b) Newkome, G. R.; McClure, G. L. J. Am. Chem. Soc. 1974, 96, 617-618.
17. No synthetic methods for compound 2b have been reported in the literature to date, although complexation studies by using 2b have been reported. See: (a) Newkome, G. R.; Onishi, M. J. Organomet. Chem. 1980, 198, 225-229; (b) Newkome, G. R.; McClure, G. L. J. Am. Chem. Soc. 1974, 96, 617-618.
18. Cai D., Hughes D.L., Verhoeven T.R. Tetrahedron Lett. 37:1996;2537-2540.
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21. max (log ε): 327 (4.90), 300 (4.70), 294 (4.71), 290 (4.70) nm. Fluorescence (ex. 326 nm) 344 nm.