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Abstrakty
Dihydrooxazole ring opening reactions in bicyclic nitroimidazodihydrooxazoles with simultaneous Williamson ethe real groups formation are described. It was found that only mutual action of K2CO3, phenol and alcohol can cause such reaction. Its mechanism consists of three steps. In a result, a series of 3-phenoxy-1-(5-alkoxy-4-ni tro- 1H-imidazol-1-yl)propan-2-ols has been obtained. The structure of new compounds was confirmed by single crystal X-ray analysis.
Wydawca
Czasopismo
Rocznik
Tom
Strony
1309--1315
Opis fizyczny
Bibliogr. 23 poz., rys.
Twórcy
autor
autor
autor
- Poznan University of Medical Sciences, Chair and Department of Organic Chemistry, Grunwaldzka 6, Poznań 60-780, Poland Tel.: +48 61 854 66 70; Fax: +48 61 854 66 80
Bibliografia
- 1. Boyer J.H., Nitroazoles, VCH Publishers Inc. Florida 1986, p.165; Martindale: The Complete Drug Reference, 34th ed., Pharmaceutical Press, London 2005, p. 105.
- 2. Allimony H.A., Saad H.A. and Mariah F.A., Indian J. Chem. Sec. B, 38, 445 (1999).
- 3. Raether W. and Hanel H., Parasitol. Res., 90 Suppl. 1, 19 (2003).
- 4. Freeman CD., Klutman N.E. and Lamp K.C, Drugs, 54, 679 (1997).
- 5. Jin C.Z., Nagasawa H., Shimamura M., Uto Y., Inayama S., Takeuchi Y, Kirk K. and Hon H., Bioorg. Med. Chem.,12, 4917 (2004).
- 6. Kasai S., Nagasawa H., YamashitaM., Masui M., KuwasakaH., Oshodani T, Uto Y, Inomata Т., Oka S., Inayama S. and Hori H., Bioorg. Med. Chem., 9,453 (2001).
- 7. Clifton E.B., Boshoff H.I.M. and Dowd C.S., Curr. Pharm. Design, 10, 3239 (2004).
- 8. Adib M., Sheibani E., Mostofi M., Ghanbary K. and Bijanzadeh H.R., Tetrahedron, 62, 3435 (2006).
- 9. Tuberculosis, 88 (2), 132 (2008), Elsevier: http://intl.elservierhealth.com/journals/tube.
- 10. Otera J. and Orita A., Patent No.: US 7, 115, 736 B2 (2006).
- 11. Li X., Manjunatha U.H., Goodwin M.B., Knox J.E., Lipiński C.A., Keller Т.Н., Barry C.E. and Dowd C.S., Bioorg. Med. Chem. Lett., 18, 2256 (2008).
- 12. Sasaki H., Haraguchi Y, Itotani M., Kuroda H., Hashizume H., Tomishige Т., Kawasaki M., Matsumoto M., Komatsu M. and Tsubouchi H., J. Med. Chem., 49, 7854 (2006).
- 13. Bhaumik K. and Akamanchi K.G., J. Heterocyclic Chem., 41, 51 (2004).
- 14. Kashima С, Arao H. and Hibi S., J. Chem. Res., 34 (1991).
- 15. Laaziri A., Uziel J. and Juge S., Tetrahedron Asym., 9, 437 (1998).
- 16. Toda F., Acc. Chem. Res., 28, 480 (1995).
- 17. Liu Z., Chen H., Cao S. and Li R., Synth. Commun., 24, 83 (1994).
- 18. Deshayes S., Liagre M., Loupy A., Luche J. and Petit A., Tetrahedron, 55, 10851 (1999).
- 19. Villa C, Genta M., Bargagna A., Mariani E. and Loupy A., Green Chem., 13, 196 (2001).
- 20. Stephenson O, J. Chem. Soc, 1571 (1954).
- 21. Pchełka В., Loupy A. and Petit A., Tetrahedron, 62, 10968 (2006) and references cited therein.
- 22. Zaprutko L., Gajdziński M., Michalska W., Pietkiewicz К., Lutomski К., Łukaszewski Z. and Wrzeciono U., Pharmazie, 44, 81 (1989).
- 23. Sheldrick G.M., SHELXS97 and SHELXL97. Realease 97-2. Universitaet Goettingen, Germany, 1997.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0028-0073