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Reaction of 1,5-Diphenyl-1,4-pentadien-3-one and 1,5-Diphenyl- 1-penten-4-yn-3-one with Monosubstituted Hydrazines

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Abstract

Phenyl- and isopropylhydrazines react with 1,5-diphenyl-1,4-pentadien-3-one to give 4,5,6,7-tetrahydroindazole derivatives instead of the expected 4,5-dihydropyrazoles. The reaction of phenylhydrazine with 1,5-diphenyl-1-penten-4-yn-3-one leads to formation of 1,5-diphenyl-3-phenylethynyl-4,5-dihydropyrazole. 2,4-Dinitrophenylhydrazine reacts with 1,5-diphenyl-1-penten-4-yn-3-one, affording the corresponding unsaturated hydrazone rather than pyrazole derivative.

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REFERENCES

  1. Kuznetsov, M.A. and Ioffe, B.V., Usp. Khim., 1989, vol. 58, no. 8, pp. 1271-1297.

    Google Scholar 

  2. Kuznetsov, M.A., Semenovskii, V.V., and Gindin, V.A., Khim. Geterotsikl. Soedin., 1991, no. 9, pp. 1176-1178.

  3. Kuznetsov, M.A., Kuznetsova, L.M., and Shantl', I.G., Russ. J. Org. Chem., 2000, vol. 36, no. 6, pp. 836-842.

    Google Scholar 

  4. Bauer, N. and Dieterle, H., Ber., 1911, vol. 44, pp. 2697-2702.

    Google Scholar 

  5. Raiford, I.C. and Manley, R.H., J. Org. Chem., 1940, vol. 5, no. 6, pp. 590-597.

    Google Scholar 

  6. Ushakov, M.I., Shusherina, N.P., and Chinaeva, A.D., Zh. Obshch. Khim., 1947, vol. 17, no. 9, pp. 1678-1683.

    Google Scholar 

  7. Gladstone, W.A.F. and Norman, R.O.C., J. Chem. Soc. C, 1966, no. 17, pp. 1536-1540.

  8. Migliorese, K.G., Tanaka, Y., and Miller, S.J., J. Org. Chem., 1974, vol. 39, no. 6, pp. 739-747.

    Google Scholar 

  9. Reihemann, S. and Watson, E.R., J. Chem. Soc., 1904, vol. 85, part I, pp. 1170-1181.

    Google Scholar 

  10. Golodnikov, G.V. and Mandel'shtam, T.V., Praktikum po organicheskomu sintezu (Laboratory Works on Organic Synthesis), Leningrad: Leningr. Gos. Univ., 1976, p. 360.

    Google Scholar 

  11. Stopskii, V.S., Sergeeva, Z.I., and Ioffe, B.V., Metody Poluch. Org. Reaktiv. Prep., 1974, no. 26, pp. 198-200.

  12. Zanina, A.S., Shergina, S.I., Sokolov, I.E., and Kotlyarevskii, I.L., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, no. 11, pp. 2551-2555.

  13. Nightingale, D. and Wadsworth, E.T., J. Am. Chem. Soc., 1947, vol. 69, no. 5, pp. 1181-1183.

    Google Scholar 

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  1. St. Petersburg State University, Universitetskii pr. 2, St. Petersburg, 198904, Russia

    E. V. Botvinnik, A. N. Blandov & M. A. Kuznetsov

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  1. E. V. Botvinnik
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  2. A. N. Blandov
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  3. M. A. Kuznetsov
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Botvinnik, E.V., Blandov, A.N. & Kuznetsov, M.A. Reaction of 1,5-Diphenyl-1,4-pentadien-3-one and 1,5-Diphenyl- 1-penten-4-yn-3-one with Monosubstituted Hydrazines. Russian Journal of Organic Chemistry 37, 421–425 (2001). https://doi.org/10.1023/A:1012448911890

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