Scope of the thermal cyclization of nonconjugated ene-yne-nitrile system: A facile synthesis of cyanofluorenol derivatives

Chemistry Letters

Volumn 37, Issue 6, 2008, Pages 662-663

  Kimura, Hidenori ^a,b   Torikai, Kohei ^a   Miyawaki, Kazuhiro ^a   Ueda, Ikuo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 48249094978     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.662     Document Type: Article

References (33)

1. For instance, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
2. b) K. C. Nicolaou, W.-M. Dai, S. C. Tsay, V. A. Estevez, W. Wrasidlo, Science 1992, 256, 1172.
3. c) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
4. d) K. K. Wang, Chem. Rev. 1996, 96, 207.
5. e) H. H. Wenk, M. Winkler, W. Sander, Angew. Chem., Int. Ed. 2003, 42, 502.
6. f) M. Gredičak, I. Jerić, Acta Pharm. 2007, 57, 133.
7. g) M. Kar, A. Basak, Chem. Rev. 2007, 107, 2861.
8. a) K. Miyawaki, R. Suzuki, T. Kawano, I. Ueda, Tetrahedron Lett. 1997, 38, 3943.
9. b) C. Ikemoto, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 5053.
10. c) K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 1998, 39, 6923.
11. d) K. Miyawaki, T. Kawano, I. Ueda, Tetrahedron Lett. 2000, 41, 1447.
12. e) T. Kawano, H. Inai, K. Miyawaki, I. Ueda, Tetrahedron Lett. 2005, 46, 1233.
13. f) T. Kawano, H. Inai, K. Miyawaki, I. Ueda, Bull. Chem. Soc. Jpn. 2006, 79, 944.
14. a) I. Ueda, Y. Sakurai, T. Kawano, Y. Wada, M. Futai, Tetrahedron Lett. 1999, 40, 319.
15. b) I. Ueda, K. Miyawaki, T. Sugane, Y. Sakurai, Y. Wada, M. Futai, Pharmazie 2000, 55, 192.
16. c) K. Torikai, Y. Otsuka, M. Nishimura, M. Sumida, T. Kawai, K. Sekiguchi, I. Ueda, Bioorg. Med. Chem., in press.
17. K. J. Stauffer, P. D. Williams, H. G. Selnick, P. G. Nantermet, C. L. Newton, C. F. Homnick, M. M. Zrada, S. D. Lewis, B. J. Lucas, J. A. Krueger, B. L. Pietrak, E. A. Lyle, R. Singh, C. Miller-Stein, R. B. White, B. Wong, A. A. Wallace, G. R. Sitko, J. J. Cook, M. A. Holahan, M. Stranieri-Michener, Y. M. Leonard, J. J. Lynch, D. R. McMasters, Y. Yan, J. Med. Chem. 2005, 48, 2282.
18. a) G. R. Heintzelman, K. M. Averill, J. H. Dodd, K. T. Demarest, Y. Tang, P. F. Jackson, PCT Int. Appl. WO 2003088963, 2003.
19. b) G. R. Heintzelman, K. M. Averill, J. H. Dodd, K. T. Demarest, Y. Tang, P. F. Jackson, U.S. Patent Appl. Publ. US 2004082578, 2004.
20. C. Safak, R. Simsek, Y. Altas, S. Boygas, K. Erol, Boll. Chim. Farm. 1997, 136, 665.
21. C. Rentzea, N. Meyer, J. Kast, P. Plath, H. Koenig, A. Harreus, U. Kardorff, M. Gerber, H. Walter, Ger. Offen. DE 4301426, 1994.
22. For the synthesis of benzofluorene cores via the thermal cyclization of non-conjugated ene-ynes, see: a) M. Schmittel, M. Strittmatter, W. A. Schenk, M. Hagel, Z. Naturforsch. 1998, 53b, 1015.
23. b) D. Rodríguez, L. Castedo, D. Domínguez, C. Saá, Tetrahedron Lett. 1999, 40, 7701.
24. c) D. Rodríguez, A. Navarro, L. Castedo, D. Domínguez, C. Saá, Org. Lett. 2000, 2, 1497.
25. For example, see: a) P. Wan, E. Krogh, J. Chem. Soc., Chem. Commun. 1985, 1207.
26. b) P. Wan, E. Krogh, J. Am. Chem. Soc. 1989, 111, 4887.
27. c) S. L. Mecklenburg, E. F. Hilinski, J. Am. Chem. Soc. 1989, 111, 5471.
28. d) G. G. Gurzadyan, S. Steenken, Chem. - Eur. J. 2001, 7, 1808.
29. H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. 1984, 96, 720.
30. F.-T. Luo, R.-T. Wang, Tetrahedron Lett. 1993, 34, 5911.
31. +].
32. Synthesis of 12 was accomplished according to the previously reported methodology: See Ref. 2a.
33. The thermal cyclization reactions of the following nonconjugated ene-yne-nitriles 15-20 failed even at 180°C in refluxing 1,2-dichlorobenzene to yield only decomposed products.