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Abstrakty
A variety of reductants for the reduction of 1-cyanoethyl-5-substituted uracil derivatives has been examined. Commonly used reductants, borane dimethyl sulphide complex, ammonium formate and sodium borohydride were applied. For the most investigated 5-substituted uracil derivatives the reduction with sodium borohydride has shown the highest effifiency when nickel(II) chloride as a catalyst has been applied. The reactions were performed in methanol at decreased temperature in the presence of di-tert-butyl carbonate as a "trapping" agent. The Boc-protected 1-(3-aminopropyl)pyrimidine- 2,4(1H,3H)- diones were synthesized in moderate to high yields.
Wydawca
Czasopismo
Rocznik
Tom
Strony
2151--2156
Opis fizyczny
Bibliogr. 22 poz., rys.
Twórcy
autor
autor
- Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland Tel.: +48 32 237 1792; fax: +48 32 237 2094
Bibliografia
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- 8. Klenke B. and Gilbert I.H., J. Org. Chem., 66, 2480 (2001).
- 9. Khurana J.M. and Kukreja G., Synth. Commun. 32, 1265 (2002).
- 10. Juarez Gea M.I., Garcia Lopez M.T., Gonzalez-Muniz R., Herrero S. and Herranz R., Tetrahedron Lett.,37, 2083 (1996).
- 11. Gowda S. and Gowda D.Ch., Tetrahedron, 58, 2211 (2002).
- 12. Carlier P.R., Lo K.M. and Williams I.D., J. Org. Chem., 60, 7511 (1995).
- 13. Johansen T.N., Greenwood J.R., Frydenvang K., Madsen U. and Krogsgaard-Larsen P., Chirality, 15, 167 (2003).
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- 16. Dolman N.P., More J.C.A., Alt A., Knauss J.L., Troop H.M., Bleakman D., Collingridge G.L. and David J.E., J. Med. Chem., 49, 2579 (2006).
- 17. Das B.K., Shibata N. and Takeuchi Y., J. Chem. Soc., Perkin Trans, 1, 197 (2002).
- 18. Shimizu T., Iwaura R., Masuda M., Hanada T. and Yase K., J. Am. Chem. Soc., 123, 5947 (2001).
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- 20. Boncel S. and Walczak K., Lett. Org. Chem., 3, 534 (2006).
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Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0023-0088