Abstract
A selective synthesis of (Z)-N-(adamantan-1-yl)carbamides by the reaction of adamantan-1-ol and nitriles in the presence of Cu catalysts was carried out. Z-Conformation of amides is established basing on X-ray diffraction analysis and 2D NMR data.
Similar content being viewed by others
References
Bagrii, E.I., Adamantany (Adamantanes), Moscow: Nauka, 1989.
Krumkalns, E., Brindle, R., Marshall, F., and Root M., J. Med. Chem., 1963, vol. 6, p.760.
Kovtun, V.Yu. and Plakhotnik, V.M., Pharm. Chem. J., 1987, vol. 21, p. 555. doi 10.1007/BF00759430
Isaev, S.D., Yurchenko, A.G., and Isaeva, S.S., Fiziol. Aktivn. Veshch., 1983, vol. 15, p.3.
Gerson, K., Tobias, D.J., Holmes, R.I., Rathbun, R.I., and Kattau, R.W., J. Med. Chem., 1967, vol. 10, p. 603. doi 10.1021/jm00316a018
Shokova, E., Mousoulou, T., Luzikov, V., and Kovalev, V., Synthesis, 1997, p. 1034.
Olah, G.A. and Balaram Gupta, B.G., J. Org. Chem., 1980, vol. 45, p. 3532.
Engel, P.S., Lee, W.-K., Marschke, G.E., and Shine, H.J., J. Org. Chem., 1987, vol. 52, p. 2813.
Haaf, W., Chem. Ber., 1963, vol. 96, p. 3359.
Sztaricskai, F., Pelyvas, J., Dinya, Z., Szilagyi, L., Gyorgydeak, Z., Hadhazy, Gy., and Vaczi, L., Pharmazie, 1975, vol. 30, p.57.
Olah, G.A., Balaram Gupta, B.G., and Narang, S.C., Synthesis, 1979, p.274.
Plakhotnik, V.M., Kovtun, V.Yu., and Yashunskii, V.G., Zh. Org. Khim., 1982, vol. 18, p. 1001.
D'Angelo, J.G., Cody, J.A., Larrabee, C., Ostrander, D.J., Rugg, K.W., and Donna Mamangun, D., Synth. Commun., 2013, vol. 43, p. 3224.
Dokli, I. and Gredicak, M., Eur. J. Org. Chem., 2015, vol. 12, p. 2727.
Lakouraj, M.M. and Mokhtary, M., Monatsh. Chem., 2009, vol. 140, p.53.
Polshettiwar, V. and Varma, R.S., Tetrahedron Lett., 2008, vol. 49, p. 2661.
Martinez, A.G., Alvarez, R.M., Vilar, E.T., Fraile, A.G., Hanack, M., and Subramanian, L.R., Tetrahedron Lett., 1989, vol. 30, p.581.
Yaragorla, S., Singh, G., Saini, P.L., and Reddy, M.K., Tetrahedron Lett., 2014, vol. 55, p. 4657. doi 10.1016/j.tetlet.2014.06.068
Posevins, D., Suta, K., and Turks, M., Eur. J. Org. Chem., 2016, vol. 7, p. 1414.
Callens, E., Burton, A.J., and Barrett, A.G.M., Tetrahedron Lett., 2006, vol. 47, p. 8699.
Firouzabadi, H., Iranpoor, N., and Khoshnood, A., Catal. Commun., 2007, vol. 9, p.529.
Jefferies, L.R. and Cook, S.P., Tetrahedron, 2014, vol. 70, p. 4204.
Khusnutdinov, R.I., Shchadneva, N.A., Mayakova, Yu.Yu., Khisamova, L.F., and Dzhemilev, U.M., Russ. J. Org. Chem., 2011, vol. 47, p. 1682. doi 10.1134/S1070428011110042
Dzhemilev, U.M., Khusnutdinov, R.I., Shchadneva, N.A., and Khisamova, L.F., RF Patent no. 2448953, 2012.
Kalkhambkar, R.G., Waters, S.N., and Laali, K.K., Tetrahedron Lett., 2011, vol. 52, p. 867. doi 10.1016/j.tetlet.2010.12.028
Jiang, F., Lin, Y.-J., Duan, H.-F., Li, Z.-H., Cao, J.-G., and Liang, D.-P., Chem. Res. Chin. Univ., 2010, vol. 26, p.384.
Pawar, D.M., Khalil, A.A., Hooks, D.R., Collins, K., Elliott, T., Stafford, J., Smith, L., and Noe, E.A., J. Am. Chem. Soc., 1998, vol. 120, p. 2108. doi 10.1021/ja9723848
CrysAlisPrO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171.NET).
Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, p.112.
Isaev, S.D., Novoselov, E.F., and Yurchenko, A.G., Zh. Org. Khim., 1985, vol. 21, p. 114.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.R. Bayguzina, A.R. Lutfullina, R.I. Khusnutdinov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1121–1126.
Rights and permissions
About this article
Cite this article
Bayguzina, A.R., Lutfullina, A.R. & Khusnutdinov, R.I. Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts. Russ J Org Chem 54, 1127–1133 (2018). https://doi.org/10.1134/S1070428018080031
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018080031