Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

A. D. Averin; M. A. Ulanovskaya; V. V. Kovalev; A. K. Buryak; B. S. Orlinson; I. A. Novakov; I. P. Beletskaya

doi:10.1134/s1070428010010069

journal article Jan 01, 2010

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

A. D. Averin

M. A. Ulanovskaya V. V. Kovalev

A. K. Buryak B. S. Orlinson

I. A. Novakov

I. P. Beletskaya

Russian Journal of Organic Chemistry Vol. 46 No. 1 pp. 64-72 · Pleiades Publishing Ltd

View at Publisher Save 10.1134/s1070428010010069

Topics

No keywords indexed for this article. Browse by subject →

References

38

[1]

Danielczyk, W., J. Neural Transm., 1995, vol. 46, p. 399.

[2]

Lyons, K.E. and Pahwa, R., Parkinson’s Desease, 2005, p. 685.

[3]

Smith, J.P., PCT Int. Appl. WO 9843625, 1998.

[4]

Leophonte, P., Bull. Acad. Nat. Med., 2005, vol. 189, p. 341.

[5]

Hughes, P.M., Olejnik, O., and Schiffman, R., US Patent Appl. Publ. no. 2005/031652, 2005.

[6]

Baxter, A., Bent, J., Bowers, K., Braddock, M., Brough, S., Fagura, M., Lawson, M., Mclnally, T., Mortimore, M., Robertson, M., Weaver, R., and Webborn, P., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 4047. 10.1016/j.bmcl.2003.08.034

[7]

Levina, M.N., Byull. Eksp. Biol. Med., 2005, vol. 139, p. 337. 10.1007/s10517-005-0288-0

[8]

Olifirov, D.I., Koshchii, V.A., and Kozlikovskii, Ya.B., Zh. Org. Khim., 1992, vol. 28, p. 182.

[9]

Kogay, B.E. and Sokolenko, W.A., Tetrahedron Lett., 1983, vol. 24, p. 613. 10.1016/s0040-4039(00)81478-1

[10]

Stepanov, F.N. and Stolyarov, Z.E., Zh. Org. Khim., 1969, vol. 5, p. 537.

[11]

Quach, T.D. and Batey, R.A., Org. Lett., 2003, vol. 5, p. 4397. 10.1021/ol035681s

[12]

Kazimierczuk, Z., Lasek, W., and Sikorska, A., PCT Int. Appl. WO 2001074778, 2001.

[13]

Kazimierczuk, Z., Gorska, A., Switaj, T., and Lasek, W., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1197. 10.1016/s0960-894x(01)00174-3

[14]

Morton, C., O’shanghnessy, P., and Scott, P., Chem. Commun., 2000, p. 2099. 10.1039/b006603f

[15]

Seredenin, S.V., Badyshtov, B.A., Voronina, T.A., Neznamov, G.G., Kozlovskaya, M.M., Levina, M.N., Rybina, I.V., Yarkova, M.A., and Pyatin, B.M., Russian Patent no.2261709, 2005.

[16]

Morozov, I.S., Klimova, N.V., Lavrova, L.N., Avdyunina, N.I., Pyatin, B.M., Troitskaya, V.S., and By- kov, N.P., Pharm. Chem. J., 1998, vol. 32, p. 3. 10.1007/bf02464216

[17]

Khamidova, T.V., Seredinceva, N.V., and Ju, L.T., Proc. 2nd Int. Congr. Vascular Dementia, 2002, p. 241.

[18]

Bugaeva, L.I., Verovskii, V.E., Lezhitsa, I.N., Kuzubova, E.A., and Spasov, A.A., Eksp. Klin. Farmakol., 2001, vol. 64, no. 5, p. 7.

[19]

Kuzubova, E.A., Bugaeva, L.I., and Spasov, A.A., Eksp. Klin. Farmakol., 2004, vol. 67, no. 3, p. 34.

[20]

Khamidova, T.V., Chigirinskii, Yu.L., and Morozov, L.S., Eksp. Klin. Farmakol., 2005, vol. 68, no. 3, p. 26.

[21]

Lezhitsa, I.N., Spasov, A.A., and Bugaeva, L.I., Neuro- toxicol. Teratol., 2001, vol. 23, p. 213. 10.1016/s0892-0362(01)00119-2

[22]

Lezhitsa, I.N., Bugaeva, L.I., Spasov, A.A., and Morozov, I.S., Eksp. Klin. Farmakol., 1999, vol. 62, no. 6, p. 39.

[23]

Vakhitova, Yu.V., Yamidanov, R.S., and Seredenin, S.B., Eksp. Klin. Farmakol., 2004, vol. 67, no. 4, p. 7.

[24]

Morozov, I.S., Efimova, L.P., and Kryzhanovskii, S.A., Eksp. Klin. Farmakol., 2000, vol. 63, no. 1, p. 33.

[25]

Bugaeva, L.I., Spasov, A.A., and Morozov, I.S., Eksp. Klin. Farmakol., 1999, vol. 62, no. 4, p. 40.

[26]

Morozov, I.S., Artsimovich, N.G., Fadeeva, T.A., Klimova, N.V., Galushina, T.S., Matvienko, M.A., Pyatin, B.M., Zaitseva, N.M., and Seredenin, S.B., USSR Patent no. 1826906, 1993.

[27]

Galushina, T.S., Fadeeva, T.A., and Artsimovich, N.G., Immunologiya (Moscow), 1996, no. 4, p. 28.

[28]

Averin, A.D., Shukhaev, A.V., Golub, S.L., Buryak, A.K., and Beletskaya, I.P., Synthesis, 2007, p. 2995. 10.1055/s-2007-990779

[29]

Averin, A.D., Ulanovskaya, O.A., Pleshkova, N.A., Borisenko, A.A., and Beletskaya, I.P., Collect. Czech. Chem. Commun., 2007, vol. 72, p. 785. 10.1135/cccc20070785

[30]

Averin, A.D., Ulanovskaya, O.A., Fedotenko, I.A., Borisenko, A.A., Serebryakova, M.V., and Beletskaya, I.P., Helv. Chim. Acta, 2005, vol. 88, p. 1983. 10.1002/hlca.200590152

[31]

Beletskaya, I.P., Bessmertnykh, A.G., Averin, A.D., Denat, F., and Guilard, R., Eur. J. Org. Chem., 2005, p. 281. 10.1002/ejoc.200400456

[32]

Averin, A.D., Ranyuk, E.R., Golub, S.L., Buryak, A.K., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Synthesis, 2007, p. 2215. 10.1055/s-2007-983760

[33]

Ranyuk, E.R., Averin, A.D., Buryak, A.K., Savel’-ev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2009, vol. 45, p. 1555. 10.1134/s1070428009100236

[34]

Wolfe, J.P. and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1144. 10.1021/jo9916986

[35]

Wolfe, J.P., Tomori, H., Sadighi, J.P., Yin, J., and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1158. 10.1021/jo991699y

[36]

Jirgensons, A., Kauss, V., Kalvinsh, I., and Gold, M., Synthesis, 2000, p. 1709. 10.1055/s-2000-8208

[37]

Lavrova, L.N., Klimova, N.V., Shmar’yan, M.I., Ul’ya-nova, O.V., Vikhlyaev, Yu.I., and Skoldinov, A.P., Zh. Org. Khim., 1974, vol. 10, p. 761.

[38]

Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J.J., and Ibers, J.A., J. Organomet. Chem., 1974, vol. 65, p. 253. 10.1016/s0022-328x(00)91277-4

Cited By

10

Arylation of adamantanamines: VI. Palladium-catalyzed arylation of amines and diamines of the adamantane series with 3-bromopyridine

A. D. Averin, T. Yu. Baranova · 2013

Russian Journal of Organic Chemistr...

Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

A. D. Averin, M. A. Ulanovskaya · 2011

Russian Journal of Organic Chemistr...

Metrics

10

Citations

38

References

Details

Published: Jan 01, 2010
Vol/Issue: 46(1)
Pages: 64-72
License: View

Authors

Cite This Article

A. D. Averin, M. A. Ulanovskaya, V. V. Kovalev, et al. (2010). Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes. Russian Journal of Organic Chemistry, 46(1), 64-72. https://doi.org/10.1134/s1070428010010069

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

You May Also Like