Highly regio-and stereoselective photocycloaddition between coumarin and thymine by molecular recognition

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8523-8526

  Mori, Keiji ^a   Murai, Osamu ^a   Hashimoto, Shigeki ^a   Nakamura, Yushin ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN; THYMINE;

ARTICLE; HYDROGEN BOND; IN VITRO STUDY; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY;

EID: 0030592778     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01981-8     Document Type: Article

References (19)

1. 1. Buckingham, A. D.; Legon, A. C.; Roberts, S. M. Principles of Molecular Recognition; Brackei A & P. Glasgow, 1993. Dugas, H. Bioorganic Chemistry; Springer New York, 1996. Lehn, J. M. Angew. Chem. Int. Ed. Engl., 1988, 27, 89.
2. 1. Buckingham, A. D.; Legon, A. C.; Roberts, S. M. Principles of Molecular Recognition; Brackei A & P. Glasgow, 1993. Dugas, H. Bioorganic Chemistry; Springer New York, 1996. Lehn, J. M. Angew. Chem. Int. Ed. Engl., 1988, 27, 89.
3. 1. Buckingham, A. D.; Legon, A. C.; Roberts, S. M. Principles of Molecular Recognition; Brackei A & P. Glasgow, 1993. Dugas, H. Bioorganic Chemistry; Springer New York, 1996. Lehn, J. M. Angew. Chem. Int. Ed. Engl., 1988, 27, 89.
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8. 6. Shim, S. C.; Chae, S. C. Photochem. Photobiol., 1979, 30, 349. Kanne, S. C.; Straub, K.; Hearst, J. E.; Rapoport, H. J. Am. Chem. Soc., 1982, 104. 6754. Shim, S. C.; Kim, Y. Z. Photochem. Photobiol., 1983, 38,265. Miolo, G.; Lucchini, V.; Rodighiero, P.; Dall'Acqua, R.; Caffieri, S. Photochem. Photobiol., 1994, 59, 277
9. 6. Shim, S. C.; Chae, S. C. Photochem. Photobiol., 1979, 30, 349. Kanne, S. C.; Straub, K.; Hearst, J. E.; Rapoport, H. J. Am. Chem. Soc., 1982, 104. 6754. Shim, S. C.; Kim, Y. Z. Photochem. Photobiol., 1983, 38,265. Miolo, G.; Lucchini, V.; Rodighiero, P.; Dall'Acqua, R.; Caffieri, S. Photochem. Photobiol., 1994, 59, 277
10. 6. Shim, S. C.; Chae, S. C. Photochem. Photobiol., 1979, 30, 349. Kanne, S. C.; Straub, K.; Hearst, J. E.; Rapoport, H. J. Am. Chem. Soc., 1982, 104. 6754. Shim, S. C.; Kim, Y. Z. Photochem. Photobiol., 1983, 38,265. Miolo, G.; Lucchini, V.; Rodighiero, P.; Dall'Acqua, R.; Caffieri, S. Photochem. Photobiol., 1994, 59, 277
11. 6. Shim, S. C.; Chae, S. C. Photochem. Photobiol., 1979, 30, 349. Kanne, S. C.; Straub, K.; Hearst, J. E.; Rapoport, H. J. Am. Chem. Soc., 1982, 104. 6754. Shim, S. C.; Kim, Y. Z. Photochem. Photobiol., 1983, 38,265. Miolo, G.; Lucchini, V.; Rodighiero, P.; Dall'Acqua, R.; Caffieri, S. Photochem. Photobiol., 1994, 59, 277
12. -1 for the anti complexes, respectively.
13. 1H NMR spectra.
14. 6; C, 65.79; H, 5.52; N, 3.65, Found; C, 65.72; H, 5.49; N, 3.62.
15. 8; C, 63.69; H, 6.24; N, 7.43, Found; C, 63.51; H, 6.19; N, 7.12.
16. 8; C, 63.69; H, 6.24; N, 7.43, Found; C, 63.71; H, 6.41; N, 7.28.
17. 6; C, 62.17; H, 5.74; N, 7.25, Found; C, 62.22; H, 5.69; N, 7.20.
18. 2O (44 : 56 →32 : 68, 15 min), detection at 240 nm for 4 ,5 and 6 or 360 nm for 1 and 2. The compounds were separated and quantitatively determined by HPLC under these conditions.
19. 11. Benzene as solvent would be preferable for hydrogen bonding formation to acetonitrile due to its small dielectric constant.