Study on the Synthesis, Reduction and Reductive Amination of Nitroindan-1-ones. Preparation of N-beta-Hydroxyethyl Derivatives of 6-Aminoindan-1-one and Indan-1,6-diamine

• Autorzy: Wodnicka A. , Kwiecień H.
• Języki publikacji: EN

Abstrakty

EN

Synthesis of 6-aminoindan-1-one and 7-amino-5,6-dimethoxyindan-1-one by nitration of corresponding indanones, followed by selective palladium catalyzed reduction under mild conditions has been described. Reactions of the amines with oxirane leading to N,N-bis-(beta-hydroxyethyl) derivatives were performed. The study of reductive amination of 6-nitroindan-1-one and 5,6-dimethoxy-7-nitroindan-1-one via azines to the corresponding amines as well as synthesis of N,N-bis-(beta-hydroxyethyl) derivatives of the amines was also described.

Słowa kluczowe

EN

indan-1-one; indan; amine; nitration; reduction; reductive amination

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2008
• Tom: Vol. 82, nr 11
• Strony: 2133--2140
• Opis fizyczny: Bibliogr. 13 poz., rys.

Twórcy

autor

Wodnicka A.

autor

Kwiecień H.

• Institute of Organic Technology, Technical University of Szczecin, Al. Piastów 42, 71-065 Szczecin, Poland,

Bibliografia

• 1. Hasbun J.A., Barker K.K. and Mertes M.P., J. Med. Chem., 16, 847 (1973).
• 2. Li C.-S., Black C., Chan C.-C, Ford-Hutchinson A. W., Gauthier J.-Y., Gordon R., Guay D., Kargman S.,Lau C.K., Mancini J., Ouimet N., Roy R, Vickers R, Wong E., Young R.N., Zamboni R. and Prasit R, J. Med. Chem., 38, 4897 (1995).
• 3. Guay D.R.R, Am. J. Geriatr. Pharmacother., 4(4), 330 (2006).
• 4. Akao Y, Maruyama W., Yi H., Shamoto-Nagai M., Youdim M.B.H. and Naoi M., Neurosci. Lett., 326,105 (2002).
• 5. Youdim M.B.H., Amit T., Falach-Vogev M., Am O.B., Maruyama W. and Naoi M., Biochem. Pharmacol., 66, 1635 (2003).
• 6. Am O.B., Amit T. and Youdim M.B.H., Neurosci. Lett., 355, 169 (2004).
• 7. Binda C., Hubalek R, Li M., Herzig Y, Sterling J., Edmondson D.E. and Mattevi A., J. Med. Chem., 48(26), 8148 (2005).
• 8. Leoni L.M., Hamel E., Genini D., Shih H., Carrera C.J., Cottam H.B. and Carson D.A., J. Natl. Cancer Inst., 92(3), 217 (2000).
• 9. Shih H., Deng L., Carrera C.J., Adachi S., Cottam H.B. and Carson D.A., Bioorg. Med. Chem. Lett., 10,487 (2000).
• 10. Kwiecień H. and Szychowska M., Synth. Commun., 37, 3599 (2007).
• 11. Ingold C.K. and Piggott H.A., J. Chem. Soc., 123, 1475 (1923).
• 12. Wan R, Davis M.J. and Teo M.A., J. Org. Chem., 54(6), 1354 (1989).
• 13. Musso D.L., Cochran F.R., Kelley J.L., McLean E.W., Selph J.L., Rigdon G.C., Orr G.R, Davis R.G.,Cooper B.R., Styles V.L., Thompson J.B. and Hall W.R., J. Med. Chem., 43(3), 399 (2003).