Abstract
An efficient procedure have been developed for the selective reduction of the carbonyl group in phenyl trichlorovinyl ketone and aryl trichloroallyl ketones by the action of NaBH4 in propan-2-ol to obtain the corresponding alcohols. The hydroxy group in the latter was converted into amino by the Ritter reaction. Treatment of the alcohols and amines with 5-phenylisoxazole-3-carbonyl chloride and 4,5-dichloroisothiazole-3-carbonyl chloride gave the corresponding esters and amides, and condensation of the amines with aromatic aldehydes afforded Schiff bases.
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Pohland, A.E. and Benson, W.R., Chem. Rev., 1966, vol. 66, p. 161.
Kaberdin, R.V., Potkin, V.I., and Petkevich, S.K., Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk, 2006, no. 2, p. 100.
Levkovskaya, G.G., Bozhenkov, G.V., and Mirskova, A.N., Selected Methods for Synthesis and Modification of Heterocycles, Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 2; Moiseev, I.K., Makarova, N.V. and Zemtsova, M.N., Izv. Vyssh. Ucheb. Zaved., Ser. Khim. Khim. Tekhnol., 2007, vol. 59, no. 1, p. 3.
Lemke, T.L., Review of Organic Functional Groups: Introduction to Medicinal Organic Chemistry, Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health, 2012, 5th ed., p. 198.
Pilgram, K. and Hass, K., J. Med. Chem., 1975, vol. 18, p. 1204.
Potkin, V.I., Kaberdin, R.V., Petkevich, S.K., and Kurman, P.V., Russ. J. Org. Chem., 2002, vol. 38, p. 1099.
Levkovskaya, G.G., Kobelevskaya, V.A., Rudyakova, E.V., Khanh, Q.H., Samultsev, D.O., and Rozentsveig, I.B., Tetrahedron, 2011, vol. 67, p. 1844.
Savosik, V.A., Rudyakova, E.V., Albanov, A.I., Bozhenkov, G.V., and Levkovskaya, G.G., Russ. J. Org. Chem., 2009, vol. 45, p. 617.
Takhistov, V.V., Prakticheskaya mass-spektrometriya organicheskikh soedinenii (Practical Mass Spectrometry of Organic Compounds), Leningrad: Leningr. Gos. Univ., 1977; Takhistov, V.V., Rodin, A.A., and Maksimova, B.N., Russ. Chem. Rev., 1991, vol. 60, no. 10, p. 1101.
Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Name Reactions in Organic Chemistry), Moscow: Khimiya, 1976; Polla, E., Bull. Soc. Chim. Belg., 1985, vol. 94, p. 81.
Brown, D.W., Floyd, A.J., and Sainsbury, M., Organic Spectroscopy, Chichester: Wiley, 1988. Translated under the title Spektroskopiya organicheskikh veshchestv, Moscow: Mir, 1992, p. 169.
Shailaja, M., Manjula, A., and Vittal Rao, B., Indian J. Chem., Sect. B, 2011, vol. 50, p. 214.
Clerici, F., Gelmi, M.L., Pellegrino, S., and Pocar, D., Bioactive Heterocycles III, Berlin: Springer, 2007, vol. 9, p. 179.
Potkin, V.I., Zubenko, Yu.A., Bykhovetz, A.I., Zolotar, R.M., and Goncharuk, V.M., Nat. Prod. Commun., 2009, vol. 4, p. 1205.
Potkin, V.I., Bykhovets, A.I., Lakhvich, F.A., Nechai, N.I., Zolotar’, R.M., Goncharuk, V.M., Zubenko, Yu.S., and Vashkevich, E.V., Belarusian Patent no. 12 039, 2007; Ofits. Byull., 2009, no. 3, p. 42.
Azometiny. Stroenie, svoistva, primenenie (Schiff Bases. Structure, Properties, and Application), Zhdanov, Yu.A., Ed., Rostov-on-Don: Rostov. Gos. Univ., 1974.
Dikusar, E.A., Potkin, V.I., and Kozlov, N.G., Benzal’-degidy vanilinovogo ryada. Sintez proizvodnykh, primenenie i biologicheskaya aktivnost’ (Benzaldehydes of the Vanillin Series. Synthesis of Derivatives, Application, and Biological Activity), Saarbrücken, Germany: LAP LAMBERT Academic, 2012; Durant, S. and Karran, P., Nucleic Acids Res., 2003, vol. 31, p. 5501.
Dyer, J.R., Applications of Absorption Spectroscopy of Organic Compounds, Englewood Cliffs: Prentice-Hall, 1965. Translated under the title Prilozheniya absorbtsionnoi spektroskopii organicheskikh soedinenii, Moscow: Khimiya, 1970, p. 92.
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Original Russian Text © V.I. Potkin, S.K. Petkevich, A.V. Kletskov, E.A. Dikusar, I.B. Rozentsveig, G.G. Levkovskaya, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 10, pp. 1430–1439.
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Potkin, V.I., Petkevich, S.K., Kletskov, A.V. et al. Synthesis of functional derivatives of aryl trichlorovinyl (trichloroallyl) ketones via consecutive transformations of the carbonyl group. Russ J Org Chem 50, 1412–1421 (2014). https://doi.org/10.1134/S1070428014100042
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DOI: https://doi.org/10.1134/S1070428014100042