Novel synthesis and properties of [n](2,4)pyridino- phanes and [n](2,4)quinolinophanes

Heterocycles

Volumn 51, Issue 5, 1999, Pages 983-987

  Miyabara, Hideo ^a   Takayasu, Tohru ^a   Nitta, Makoto ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINOL; QUINOLINOL DERIVATIVE;

ALKYLATION; AROMATIZATION; ARTICLE; DRUG SYNTHESIS; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMOREGULATION;

EID: 0033133880     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8513     Document Type: Article

References (26)

1. The older literature has been reviewed: P. M. Keehn and B. M. Rosenfeld, Cyclophanes, Academic Press, New York, 1983.
2. Review on small cyclophanes: V. V. Kane, W. N. de Wolf, and F. Bickelhaupt, Tetrahedron, 1994, 50, 4575.
3. Y. Tobe, Topics in Current Chemistry, 1994, 172, 1.
4. G. J. Bodwell, Angew. Chem. Int. Ed. Engl., 1996, 35, 2085.
5. T. Kobayashi and M. Nitta, Bull. Chem. Soc. Jpn., 1985, 58, 3099.
6. H. Gerlach and E. Huber, Helv. Chim. Acta, 1968, 51, 3099; N. Kanomata and T. Nakata, Angew. Chem., Int. Ed. Engl., 1997, 36, 1207.
7. H. Gerlach and E. Huber, Helv. Chim. Acta, 1968, 51, 3099; N. Kanomata and T. Nakata, Angew. Chem., Int. Ed. Engl., 1997, 36, 1207.
8. D. Dhanakand C. B. Reese, J. Chem. Soc., Perkin Trans. 1, 1987, 2829.
9. K. Biemann, G. Büchi, and B. H. Walker, J. Am. Chem. Soc., 1957, 79, 5558; S. Fujita and H. Nozaki, Bull. Chem. Soc. Jpn., 1971, 44, 2827; K. Tamao, S. Kodama, T. Nakatsuka, Y. Kiso, and M. Kumada, J. Am. Chem. Soc., 1975, 97, 4405.
10. K. Biemann, G. Büchi, and B. H. Walker, J. Am. Chem. Soc., 1957, 79, 5558; S. Fujita and H. Nozaki, Bull. Chem. Soc. Jpn., 1971, 44, 2827; K. Tamao, S. Kodama, T. Nakatsuka, Y. Kiso, and M. Kumada, J. Am. Chem. Soc., 1975, 97, 4405.
11. K. Biemann, G. Büchi, and B. H. Walker, J. Am. Chem. Soc., 1957, 79, 5558; S. Fujita and H. Nozaki, Bull. Chem. Soc. Jpn., 1971, 44, 2827; K. Tamao, S. Kodama, T. Nakatsuka, Y. Kiso, and M. Kumada, J. Am. Chem. Soc., 1975, 97, 4405.
12. A. Balaban, Tetrahedron Lett., 1968, 4643; A. Balaban, Tetrahedron Lett., 1978, 5055.
13. A. Balaban, Tetrahedron Lett., 1968, 4643; A. Balaban, Tetrahedron Lett., 1978, 5055.
14. W. E. Parham, R. W. Davenport, and J. B. Biasotti, Tetrahedron Lett., 1969, 557; W. E. Parham, K. B. Sloan, and J. B. Biasotii, Tetrahedron, 1971, 27, 5767.
15. W. E. Parham, R. W. Davenport, and J. B. Biasotti, Tetrahedron Lett., 1969, 557; W. E. Parham, K. B. Sloan, and J. B. Biasotii, Tetrahedron, 1971, 27, 5767.
16. W. E. Parham, R. Davenport, and J. B. Biasotii, J. Org. Chem., 1970, 35, 3775.
17. N. Kanomata and M. Nitta, J. Chem. Soc., Perkin Trans. 1, 1990, 1119.
18. M. Nitta, T. Akie, and Y. Iino, J. Org. Chem., 1994, 59, 1309.
19. M. Nitta, Reviews on Heteroatom Chemistry, 1993, 9, 87; and references cited therein.
20. T. Mulamba, R. E. B. Garré, D. Séraphin, E. Noé, C. C. Fagnère, J. Hérin, J. Laronze, J. Sapi, R. Barrel, J. -Y. Laronze, and J. Lévy, Heterocycles, 1995, 41, 29; and references cited therein.
21. Elemental analyses and spectroscopic data are satisfactory for all new compounds in this paper.
22. 3, 400MHz) 0.86-0.91 (3H, m), 1.28-1.42 (6H, m), 1.67-1.76 (2H, m), 2.19 (2H, quint, J=6.4 Hz), 2.67 (2H, t, J=6.6 Hz), 2.81 (2H, t, J=7.9 Hz), 3.12 (2H, t, J= 6.2 Hz), 7.13 (1H, d, J=8.1 Hz), 8.18 (1H, d, J=8.1 Hz).
23. N. L. Allinger, T. J. Walter, and M. G Newton, J. Am. Chem. Soc., 1974, 96, 4588; S. Hirano, H. Hara, T. Hiyama, S. Fujita, and H. Nozaki, Tetrahedron, 1975, 31, 2219.
24. N. L. Allinger, T. J. Walter, and M. G Newton, J. Am. Chem. Soc., 1974, 96, 4588; S. Hirano, H. Hara, T. Hiyama, S. Fujita, and H. Nozaki, Tetrahedron, 1975, 31, 2219.
25. N. L. Allinger, J. T. Sprague, and T. Liljefors, J. Am. Chem. Soc., 1974, 96, 5100.
26. J. I. Seeman, Pure & Appl. Chem., 1987, 59, 1661; and references cited therein.