Synthesis of new macrocyclic ligands containing benzopyran system

Bulletin of the Korean Chemical Society

Volumn 22, Issue 8, 2001, Pages 917-920

  Yoo, Sung eun ^a   Jeon, In Cheol ^b   Yi, Kyu Yang ^b   Kim, Kwan Soo ^b  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Yonsei University   (South Korea)

Author keywords

Azacrown; Benzopyran; Intramolecular cyclization; Macrocyclic ligands

Indexed keywords

BENZOPYRAN DERIVATIVE; HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DIMERIZATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0035538928     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
2. (b) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
3. (a) Gryko, D. T.; Piatek, P.; Jurczak, J. Tetrahedron 1997, 53, 7957.
4. (b) Mertes, M. P.; Mertes, K. B. Acc. Chem. Res. 1990, 23, 413.
5. (c) Krakowiak, K. E.; Bradshow, J. S.; Izatt, R. M. Synlett 1993, 612.
6. (d) Zang, X.-X.; Buchwald, S. L. J. Org. Chem. 2000, 65, 8027.
7. (e) Chadwick, D. J.; Cliffe, I. A.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. I 1984, 1707.
8. (a) Schultz, R. A.; Dishong, D. M.; Gokel, G. W. J. Am. Chem. Soc. 1982, 104, 625.
9. (b) Galto, V. J.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 8240.
10. (c) Katritzky, A. R.; Belyakov, S. A.; Sorochinsky, A. E. J. Org. Chem. 1996, 61, 7585.
11. (a) Murakami, U.; Kikuchi, J.-i.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721.
12. (b) Hu, X.; He, J.; Chan, A. S. C.; Han, X.; Cheng, J.-P. Tetrahedron: Asymmetry 1999, 10, 2685.
13. (a) Cram, D. J.; Cram, J. M. Science 1974, 183, 803.
14. (b) Cram, D. J. Science 1988, 240, 760.
15. (c) Chu, I.-H.; Dearden, D. V.; Bradshaw, J. S.; Huszthy, P.; Izatt, R. M. J. Am. Chem. Soc. 1993, 115, 4318.
16. (a) Kyba, E. B.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Cram, D. J. J. Am. Chem. Soc. 1993, 115, 4318.
17. (b) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713.
18. (c) Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313.
19. (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
20. (b) Nicolaou, K. C.; Pfefferkorn, S.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G.-Q. J. Am. Chem. Soc. 2000, 122, 9968.
21. (a) Ashwood, V. A.; Buckingham, R. E.; Cassidy, F.; Evans, J. M.; Faruk, E. A.; Hamilton, T. C.; Nash, D. J.; Stemp, G.; Willcocks, K. J. Med. Chem. 1986, 29, 2194.
22. (b) Atwal, K. S.; Grover, G. J.; Ferrara, F. N.; Ahmed, S. Z.; Sleph, P. G.; Dzwonczyk, S.; Normandin, D. E. J. Med. Chem. 1995, 38, 1966.
23. (a) Shin, H. S.; Seo, H. W.; Yoo, S.-E.; Lee, B. H. Pharmacology 1998, 56, 111.
24. (b) Lee, B. H.; Yoo, S.-E.; Shin, H. S. J. of Cardiovascular Pharmacol, 1998, 31, 85.
25. (c) Yoo, S.-E.; Suh, J. H.; Lee, S. J.; Jeong, N. Bioorg. Med. Chem. Lett. 1992, 2, 381.
26. Kabbe, H.-J.; Widdig, A. Angew. Chem. Int. Ed. Engl. 1982, 21, 247.
27. Yamada, S.; Morizono, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329.
28. (a) Adams, J.; Frenette, R.; Belley, M.; Chibante, F.; Springer, J. P. J. Am. Chem. Soc. 1987, 109, 5432.
29. (b) Wiberg, K. B.; Furtek, B. L.; Olli, L. K. J. Am. Chem. Soc. 1979, 101, 7675.
30. Kim, S.; Lee, J. I.; Yi, K. Y. Bull. Chem. Soc. Jpn. 1985, 58, 3570.
31. Desei, M. C.; Stramiello, L. M. S. Tetrahedron Lett. 1993, 34, 7685.
32. Mukaiyama, T. Angew. Chem. Int. Ed. Engl. 1976, 15, 94.
33. Brown, H. C.; Heim, P.; Yoon, N. M. J. Am. Chem. Soc. 1970, 92, 1637.