Synthesis of 1-benzoxepin-5-ones (ols) from salicylaldehydes via ring-closing metathesis

Arkivoc

Volumn 2008, Issue 2, 2008, Pages 172-182

  Li, Sie Rong ^a   Chen, Hsing Ming ^b   Chen, Liang Yeu ^a   Tsai, Jui Chi ^a   Chen, Po Yuan ^a   Hsu, Sodio Chih Neng ^a   Wang, Eng Chi ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b FOOYIN UNIVERSITY   (Taiwan)

Author keywords

1 benzoxepin 5 ols; 1 benzoxepin 5 ones; Ring closing metathesis; Salicylaldehydes

Indexed keywords

EID: 39049110580     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.219     Document Type: Article

References (22)

1. Dumontet, V.; Thoison, O.; Omobuwajo, O. R.; Martin, M.-T.; Perromat, G.; Chiaroni, Angele; Riche, C.; Pais, M.; Sevenet, T.; Hadi, A. H. Tetrahedron 1996, 52, 6931.
2. (a) Tandon, V. K.; Singh, K. A.; Awasthi, A. K.; Khanna, J. M.; Lal, B.; Anand, N. Bioorg. & Med. Chem. Lett. 2004, 14, 2867.
3. (b) Lin, Y.-L.; Kuo, H.-S.; Wang, Y.-W.; Huang, S.-T. Tetrahedron 2003, 59, 1277.
4. (c) Kaupmann, W.; Ohlendorf, H. W.; Wolf, K. U. Eur. J. Med. Chem. 1985, 20, 207.
5. (d) Albrecht, G.; Ecker, G.; Tumova, I. Sci. Pharm. 1993, 61, 161.
6. (e) Purcell, T.; Zard, L. Eur. Pat. Appl. 198,762, 1986 ; Chem. Abstr. 1987, 107, 198114.
7. (f) Balme, G.; Coudanne, I.; Desbordes, P.; Huser, N.; Lemaire, P.; Mousques, A.; Nivlet, A.; Vors, J.-P. PCT Int. Appl. WO 2003014104, 2003 ; Chem. Abstr. 2003, 138, 187654.
8. (g) Ryabukhin, S. V.; Volochnyuk, D. M.; Plaskon, A. S.; Naumchik, V. S.; Tolmachev, A. A. Synthesis 2007, 1214.
9. Hofmann, H.; Djafari, H. Z. Nat. forsch., B, J. Chem. Sci. 1989, 44, 220.
10. Tatsuoka, T.; Imao, K.; Suzuki, K.; Shibata, M.; Satoh, F.; Miyano, S.; Sumoto, K. Heterocycles 1990, 30, 749.
11. Hasegawa, E.; Tsuchida, H.; Tamura, M. Chem. Lett. 2005, 34, 1688.
12. Hofmann, H.; Djafari, H. Liebigs Ann. Chem. 1985, 3, 599.
13. von Angerer, S. Science of Synthesis 2004, 17, 653.
14. (a) Grubbs, R. H. Angew. Chem. Int. Ed. 2006, 45, 3760.
15. (b) Briggs, T. F.; Dudley, G. B. Tetrahedron Lett. 2005, 46, 7793.
16. (a) Pospisil, J.; Potacek, M. Tetrahedron, 2007, 63, 337 and literature citied therein.
17. (b) Orlek, B. S.; Sammes, P. G.; Weller, D. J. Tetrahedron 1993, 49, 8179.
18. Nelson, W. L.; Burke, T. R., Jr. J. Med. Chem. 1979, 22, 1082.
19. Fuerstner, A.; Aiessa, C. J. Am. Chem. Soc. 2006, 128, 6306.
20. Campi, E. M.; Jackson, W. R.; McCubbin, Q. J.; Trnacek, A. E. Aust. J. Chem. 1996, 49, 219.
21. Lee, J. I.; Lee, H. S.; Kim, B. H. Synth. Commun. 1996, 26, 3201.
22. Martin, S. F.; Garrison, P. J. J. Org. Chem. 1982, 47, 1513.