Reductive transformations of Schiff bases in the synthesis of functionally substituted heteroaromatic amines
详细信息 查看全文
- 作者：Zh. V. Ignatovich (1)
A. P. Kadutskii (2)
E. V. Koroleva (1)
A. V. Baranovskii (3)
K. N. Gusak (1) - 刊名：Russian Journal of Organic Chemistry
- 出版年：2009
- 出版时间：July 2009
- 年：2009
- 卷：45
- 期：7
- 页码：1070-1078
- 全文大小：247KB
- 参考文献：1. Kouznetsov, V.V., Vargas Mendes, L.Y., and Melendez Gomez, C.M., / Curr. Org. Chem., 2005, vol. 9, p. 141. p://dx.doi.org/10.2174/1385272053369196">CrossRef
2. Lukevics, E., Segal, I., Zablotskaya, A., and Germane, S., / Molecules, 1997, p. 180.
3. Francis, C.L., Williamson, N.M., and Ward, A.D., / Synthesis, 2004, p. 2685.
4. Enguehard-Gueiffier, C., H眉bner, H., Hakmaoui, Ah., Allouchi, H., Gmeiner, P., Argiolas, A., Melis, M.R., and Gueiffier, A., / J. Med. Chem., 2006, vol. 49, p. 3938. p://dx.doi.org/10.1021/jm060166w">CrossRef
5. Romero, D.L., Busso, M., Tan, C-K., Reusser, F., Palmer, A.P.A., So, A.G., Resnick, L., and Tarplay, W.G., / Proc. Natl. Acad. Sci. USA, 1991, vol. 88, p. 8806. p://dx.doi.org/10.1073/pnas.88.19.8806">CrossRef
6. Leopoldo, M., Giorgio, P., Berardi, F., Lacivita, E., Colabuto, N.A., Perrone, R., and Tortorella, V., / J. Med. Chem., 2002, vol. 45, p. 5727. p://dx.doi.org/10.1021/jm020952a">CrossRef
7. Ignatovich, J., Gusak, K., Kozlov, N., Kovalev, V., and Koroleva, E., / Archivoc, 2008, part (ix), p. 51.
8. Szakacs, Z., Beni, S., Vagra, Z., Orfi, L., Keri, G., and Noszal, B., / J. Med. Chem., 2005, vol. 48, p. 249. p://dx.doi.org/10.1021/jm049546c">CrossRef
9. EPV Patent no. 0 564 409, 1994; / Chem. Abstr., 1994, vol. 120, no. 107 056 w.
10. Gribbl, G.W., / Chem. Soc. Rev., 1998, vol. 27, p. 395; Gribbl, G.W. and Heald, P.W., / Synthesis, 1975, p. 650. p://dx.doi.org/10.1039/a827395z">CrossRef
11. Kadutskii, A.P. and Kozlov, N.G., / Synlett, 2006, p. 3349.
12. Gusak, K.N. and Kozlov, N.G., / Russ. J. Org. Chem., 2007, vol. 43, p. 706. p://dx.doi.org/10.1134/S1070428007050119">CrossRef
13. Kozlov, N.G., Koroleva, E.V., Ignatovich, Zh.V., Gusak, K.N., and Kadutskii, A.P., / Russ. J. Org. Chem., 2007, vol. 43, p. 901. p://dx.doi.org/10.1134/S1070428007060176">CrossRef
14. Kozlov, N.S., Gusak, K.N., Serzhanina, V.A., and Krot, N.A., / Khim. Geterotsikl. Soedin., 1985, p. 1398.
15. Mashkovskii, M.D., / Lekarstvennye sredstva (Drugs), Khar鈥檏ov: Torsing, 1998, vol. 2, p. 320.
16. Balcom, D. and Furst, A., / J. Am. Chem. Soc., 1953, vol. 75, p. 4334. p://dx.doi.org/10.1021/ja01113a502">CrossRef
17. Kuznechikov, O.A., Savel鈥檈v, E.I., and Mokhov, V.M., / Internet-Vestnik Volgogr. Gos. Arkhitekt.-Stroit. Univ., Politemat. Ser., 2008, no. 1; www.vestnik.vgasu.ru.
18. Gusak, K.N., Tereshko, A.B., and Kozlov, N.G., / Russ. J. Gen. Chem., 2000, vol. 70, p. 298. - 作者单位：Zh. V. Ignatovich (1)
A. P. Kadutskii (2)
E. V. Koroleva (1)
A. V. Baranovskii (3)
K. N. Gusak (1)
1. Institute of New Materials Chemistry, National Academy of Sciences of Belarus, ul. F. Skoriny 36, Minsk, 220141, Belarus
2. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus
3. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus - ISSN：1608-3393
文摘
Schiff bases synthesized by condensation of 5- and 6-aminoquinolines, 5-amino-2-methylquinoline, nitroanilines, and pyrimidinylaminoanilines with substituted benzaldehydes and pyridinecarbaldehydes were reduced with sodium tetrahydridoborate in acetic acid to obtain the corresponding N-aryl(hetaryl)benzylamines, N-(pyridylmethyl)anilines, and N-(1,2,3,4-tetrahydroquinolyl)benzylamine derivatives. The reduction of arylhetarylimines with hydrazine hydrate in the presence of Raney nickel involved only the azomethine C=N bond, while the nitrogen-containing heteroaromatic ring remained intact. Under analogous conditions, nitrosubstituted Schiff bases and benzyl- and pyridylmethylamines were converted into previously unknown N-(aminobenzyl)quinolinamines and aryl(pyridyl)methyl-substituted phenylenediamines.