Abstract
Reactions of arylchloropyruvic acids esters with aryl- and hetarylhydrazines give rise to pyrazolinedione hydrazones as a result of a tandem condensation of the substituted hydrazines with arylchloropyruvates. In contrast to this process in reaction with hydrazine hydrate a ready reduction unexpectedly occurs by Kizhner-Wolff mechanism affording 3-hydroxydihydrocinnamic acid hydrazide as the principal product. The isomeric arylglycidate reacts along the same pattern.
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REFERENCES
Kitaev, Yu.P and Buzykin, B.N., Gidrazony (Hydrazons), Kost, A.N., Ed., Moscow: Nauka, 1974, vol. 262, p. 370.
Ramirez, F. and Kirby, J., J. Am. Chem. Soc., 1953, vol. 23, p. 6026.
Pritzkow, W., Z. Chem., 1970, vol. 10, p. 330.
Hassner, A. and Catsonlaccos, P., Chem. Commun., 1967, p. 121.
Simon, H., Moldenhauer, W., and Kraus, A., Chem. Ber., 1969, vol. 102, p. 2777.
Stickler, W.C. and Hoffman, W.C., Angew. Chem., 1970, vol. 82, p. 254.
Roeding, A. and Wenzel, W., Lieb. Ann., 1969, vol. 728, p. 1.
Wharton, P.S., Dunug, S., and Krebs, L.S., J. Org. Chem., 1964, vol. 29, p. 958.
Crawford, R.J. and Tokunada, H., Canad. J. Chem., 1974, vol. 52, p. 4033.
Shvaika, O.P. and Artemov, V.N., Usp. Khim., 1972, vol. 10, p. 1788.
Slagel, R.S., J. Org. Chem., 1968, vol. 33, p. 1374.
Europe Patent 52333, 1996; Chem. Abstr., 1997, 144854g.
Shkineva, T.G., Dalinger, I.L., and Shevelev, S.A., Khim. Geterotsikl. Soed., 1995, p. 579.
Wolfrom, M.L. and Wood, H.B., J. Am. Chem. Soc., 1951, vol. 73, p. 2933.
Patai, S., The Chemistry of the Hygrazo, Azo, and Azoxy Groups, part I, 1975, p. 154.
Strakov, A.Ya., Petrova, M.V., Strakova, I.A., and Lakhovich, O.F., Khim. Geterotsikl. Soed., 1995, p. 336.
Mamedov, V.A., Valeeva, V.N., Antokhina, L.A., and Nuretdinov, I.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, p. 1422.
Mamedov, V.A., Berdnikov, E.A., Valeeva, V.N., Ismaev, I.E., Rizvanov, I.Kh., Antokhina, L.A., Nuretdinov, I.A., and Chernov, P.P., Izv. Akad. Nauk, Ser. Khim., 1993, p. 1962.
Mustakimova, L.V., Mamedov, V.A., and Levin, Ya.A., Khimiya i primenenie fosfor-, sera-, i kremniiorganicheskikh soedinenii (Chemistry and Application of Phosphor, Sulfur, and Silicon Containing Compounds), St. Petersburg, 1998, p. 107.
Singh, S.P., Kodai, D.R., Dhindsa, G.S., and Sawhney, S.N., Indian J. Chem., 1982, vol. 21B, p. 30.
Singh, S.P., Sehgal, S., Tarar, L.G., and Dhawan, S.N., Indian J. Chem., 1990, vol. 29B, p. 310.
Mahajan, M.P., Sondhi, S.M., and Ralhan, N.K., Austral. J. Chem., 1977, vol. 30, p. 2053.
Minkin, V.I., Olekhnovich, L.P., and Zhdanov, Yu.A., Molekulyarnyi dizain tautomernykh sistem (Molecular Design of Tautomeric Systems), Mikhailov, I.E., Rostov: Rostov. Gos. Univ., 1977, p. 271.
Alaka, B.V., Patnaik, D., and Rout, M.K., J. Indian Chem. Soc., 1982, vol. 69, p. 1168.
Gasteiger, J. and Herzig, Ch., Tetrahedron Lett., 1980, vol. 21, p. 2687.
Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Srystallogr. A, 1991, vol. 47, p. 744.
Straver, L.H. and Schierbeek, A.J., MolEN. Structure Determination System. 1. Program Description, Nonius, B.V., Ed., 1994.
Spek, A.L., PLATON. A Miltipurpouse Crystallographic Tool, Utrecht: Utrecht University Press, 2000, p. 214.
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 5, 2005, pp. 710–717.
Original Russian Text Copyright © 2005 by Mamedov, Mustakimova, Gubaidullin, Litvinov, Levin.
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Mamedov, V.A., Mustakimova, L.V., Gubaidullin, A.T. et al. Reactions of Isomeric Arylchloropyruvates and Glycidates with Hydrazines. Russ J Org Chem 41, 694–702 (2005). https://doi.org/10.1007/s11178-005-0228-5
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DOI: https://doi.org/10.1007/s11178-005-0228-5