Abstract
Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Clerici, F., Gelmi, M.L., Pellegrino, S., and Pocar, D., Bioactive Heterocyces III, Berlin–Heidelberg: Springer, 2007, vol. 9, p. 179.
Murugesan, N., Gu, Z., Spergel, S., Young, M., Chen, P., Mathur, A., Leith, L., Hermsmeier, M., Liu, E.C., Zhang, R., Bird, E., Waldron, T., Marino, A., Koplowitz, B., Humphreys, W.G., Chong, S., Morrison, R.A., Webb, M.L., Moreland, S., Trippodo, N., and Barrish, J.C., J. Med. Chem., 2003, vol. 46, p. 125.
Gardner, T.S., Wenis, E., and Lee, J., J. Med. Pharm. Chem., 1960, vol. 2, p. 133.
Pinto, P. and Dougados, M., Acta Reumatol. Port., 2006, vol. 31, p. 216.
Talley, J.J., Brown, D.L., Carter, J.S., Graneto, M.J., Koboldt, C.M., Masferrer, J.L., Perkins, W.E., and Rogers, R.S., J. Med. Chem., 2000, vol. 43, p. 775.
Smith, R.A., Barbosa, J., Blum, C.L., Bobko, M.A., Caringal, Y.V, Dally, R., Johnson, J.S., Katz, M.E., Kennure, N., Kingery-Wood, J., Lee, W., Lowinger, T.B., Lyons, J., Marsh, V., Rogers, D.H., Swartz, S., Walling, T., and Wild, H., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2775.
Shailaja, M., Manjula, A., and Vittal Rao, B., Indian J. Chem., 2011, vol. 50B, p. 214.
Rzeski, W., Ikonomidou, Ch., and Turski, L., Biochem. Pharmacol., 2002, vol. 64, p. 1195.
Kamal, A., Bharathi, E.V., Reddy, J.S., Ramaiah, M.J., Dastagiri, D., Reddy, K., Viswanath, A., Reddy, T.L., Shaik, T.B., Pushpavalli, S.N.C.V.L., and Bhadra, M.P., Eur. J. Med. Chem., 2011, vol. 46, p. 691.
Kulchitsky, V.A., Potkin, V.I., Zubenko, Yu.S., Chernov, A.N., Talabaev, M.V., Demidchik, Yu.E., Petkevich, S.K., Kazbanov, V.V., Gurinovich, T.A., Roeva, M.O., Grigoriev, D.G., Kletskov, A.V., and Kalunov, V.N., Med. Chem., 2012, vol. 8, p. 22.
Potkin, V.I., Bumagin, N.A., Petkevich, S.K., Lyakhov, A.S., Rudakov, D.A., Livantsov, M.V., and Golantsov, N.E., Synthesis, 2012, vol. 44, p. 151.
Potkin, V.I., Bumagin, N.A., Petkevich, S.K., Kletskov, A.V., Zubenko, Yu.S., Golantsov, N.E., Livantsov, M.V., Belov, D.S., and Veselov, I.S., Dokl. Nats. Acad. Nauk Belarusi, 2013, vol. 1, p. 67.
Bumagin, N.A., Petkevich, S.K., Kletskov, A.V., Livantsov, M.V., Golantsov, N.E., and Potkin, V.I., Chem. Heterocycl. Compd., 2014, vol. 49, p. 1515.
Kulchitsky, V.A., Alexandrova, R., Suziedelis, K., Paschkevich, S.G., and Potkin, V.I., Recent Pat. Nanomed., 2015, vol. 4, p. 82.
Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Dikusar, E.A., Zubenko, Yu.S., Zhukovskaya, N.A., Kazbanov, V.V., and Pashkevich, S.G., Russ. J. Org. Chem., 2013, vol. 49, p. 1523.
Mel’nikov, N.N., Pestitsidy. Kkhimiya, tekhnologiya i primenenie (Pesticides. Chemistry, Technology, and Application), Moscow: Khimiya, 1987.
Singh D.K., Pesticide Chemistry and Toxicology, Sharjah: Bentham Science Publishers, 2012, vol. 1.
Minbaev, B.U. and Yashnova, N.I., Fiziko-khimicheskie svoistva shiffovykh osnovanii (Physico-Chemical Properties of Schiff Bases), Alma-Ata: Nauka Kazakhskoi SSR, 1990.
Potkin, V.I., Zubenko, Yu.S., Bykhovetz, A.I., Zolotar, R.M., and Goncharuk, V.M., Nat. Prod. Commun., 2009, vol. 4, p. 1205.
Dikusar. E.A., Prostye i slozhnye efiry v linkernykh tekhnologiyakh: sovremennye aspekty molekulyarnogo dizaina–ot dushistykh veshchestv do biologicheski aktivnykh soedinenii (Ethers and Esters in Linker Technologies. Modern Aspects of Molecular Design: From Fragrant Substances to Biologically Active Compounds), Saarbrücken, Deutschland: Lambert Academic Publishing, 2014.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.I. Potkin, N.A. Bumagin, S.K. Petkevich, E.A. Dikusar, E.V. Semenova, P.V. Kurman, R.M. Zolotar’, S.G. Pashkevich, T.A. Gurinovich, V.A. Kul’chitskii, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1140–1150.
Rights and permissions
About this article
Cite this article
Potkin, V.I., Bumagin, N.A., Petkevich, S.K. et al. Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes. Russ J Org Chem 51, 1119–1130 (2015). https://doi.org/10.1134/S1070428015080102
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428015080102