The Attempts of the Cyano Group Reduction in 1-Cyanoethyl 5-Substituted Uracil Derivatives

• Autorzy: Boncel S. , Walczak K.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

reduction of cyano group; 5-substiuted uracils; nickel chloride as co-catalyst; sodium borohydride

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 12
• Strony: 2151--2156
• Opis fizyczny: Bibliogr. 22 poz., rys.

Twórcy

autor

Boncel S.

autor

Walczak K.

• Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland Tel.: [phone]; fax: [phone]

Bibliografia

• 1. Ciaccio J.A., Smrtka M., Maio W.A. and Ruando A.D., Tetrahedron Lett., 45, 7201 (2004).
• 2. Sakai N. and Matile S., Tetrahedron Lett., 38, 2613 (1997).
• 3. Ganem B. and Osby J.O., Chem. Rev., 86, 763 (1986).
• 4. Ram S. and Ehrenkaufer R.E., Synthesis, 91 (1988).
• 5. Brown H.C., Choi Y.M. and Narasimhan S., J. Org. Chem., 47, 3153 (1982).
• 6. Ogura K., Shimamura Y. and Fujita M., J. Org. Chem. 56, 2920 (1991).
• 7. Caddick S., Judd D.B., Lewis de K. A., Reich M.T. and Williams M.R.Y., Tetrahedron, 59,5417 (2003).
• 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).
• 14. Chittajallu R., Braithwaite S.R, Clarke V.R.J. and Henley J.M., Trends in Pharmacol. Sci.,10,2.6 (1999).
• 15. More J.C.A., Troop H.M. and Jane D.E., Brit. J. Pharm., 137, 1125 (2002).
• 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).
• 19. Hyrup B., Egholm M., Nielsen P.E., Wirtung P., Norden B. and Buchardt O., J. Am. Chem. Soc., 116, 7964 (1994).
• 20. Boncel S. and Walczak K., Lett. Org. Chem., 3, 534 (2006).
• 21. Periasamy M. and Thirumalaikamurr M., J. Organomet. Chem., 609, 137 (2000).
• 22. Kunesch N., Lu Y, Miet C. and Poisson J., Tetrahedron Asymmetry, 1, 707 (1990).