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Isobutyraldehyde in the Synthesis of Isopropyl-substituted 4H-Pyrans, 1,4-Dihydropyrano[2,3-c]pyrazole, 1,4-Dihydropyridines, and Cyclobutane

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Abstract

Condensation of isobutyraldehyde with CH acids, such as acetoacetanilide, dimedone, acetoacetamide, ethyl benzoylacetate, resorcinol, cyanoacetic acid, malononitrile, 3-methyl-1-ethyl-2-pyrazolin-5-one, benzoylacetone, and cyanoacetamide, in the presence of amines gave isopropyl-substituted 4H-pyrans, 1,4-dihydropyrano[2,3-c]pyrazole, 4H-benzo[b]pyranes, 1,4-dihydropyridines, and 1,1-dicyano-2-(1-cyano-1-ethoxycarbonyl)methyl-4-isopropyl-3,3-dimethylcyclobutane. The structure of the latter product was studied by X-ray diffraction analysis.

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REFERENCES

  1. Litvinov, V.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, no. 11, p. 2123.

  2. Dyachenko, V.D., Doctoral (Chem.) Dissertation, Moscow, 1998.

  3. Litvinov, V.P., Usp. Khim., 2003, vol. 72, no.1, p. 75.

    Google Scholar 

  4. Sharanin, Yu.A., Goncharenko, M.P., and Litvinov, V.P., Usp. Khim., 1998, vol. 67, no.5, p. 442.

    Google Scholar 

  5. Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 1999, no. 5, p. 579.

  6. Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Schestopalov, A.M., and Senning, A., Sulfur Reports, 1992, vol. 13, no.1, p. 1.

    Google Scholar 

  7. Comprehensive Organic Chemistry, Barton, D.H. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 1. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1982, vol. 2, p. 448.

    Google Scholar 

  8. Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1999, no. 8, p. 1099.

  9. Dyachenko, V.D., Materialy pervoi mezhdunarodnoi konferentsii “Khimiya i biologicheskaya aktivnost’ azotistykh geterotsiklov i alkaloidov” (Proc. I Int. Conf. “Chemistry and Biologic Activity of Nitrogenous Heterocyclic Compounds”), Moscow, 2001, vol. 2, p. 101.

    Google Scholar 

  10. Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1996, no. 8, p. 1094.

  11. Dyachenko, V.D., in Sbornik nauchnyh trudov “Novye dostizhe-niya v khimii karbonil’nyh soedinenii” (Coll. Sci. Works “Advances in Chemistry of Carbonyl Compounds”), Saratov, 2000, p. 60.

  12. Dyachenko, V.D., Nesterov, V.N., Krivokolysko, S.G., and Litvinov, V.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, vol. 1, p. 196.

    Google Scholar 

  13. Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, no. 11, p. 2013.

  14. Dyachenko, V.D., Krivokolysko, S.G., Nesterov, V.N., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1997, no. 12, p. 1655.

  15. Dyachenko, V.D., Nesterov, V.N., Krivokolysko, S.G., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1997, no. 6, p. 785.

  16. Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Name Reactions in Organic Chemistry), Moscow: Khimiya, 1976.

    Google Scholar 

  17. Nesterov, V.N., Shklover, V.E., Struchkov, Yu.T., Sharanin, Yu.A., Schestopalov, A.M., and Rodinovskaya, L.A., Acta Crystallogr., Sect. C, 1985, vol. 41, no.8, p. 1191.

    Google Scholar 

  18. Nesterov, V.N. and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 1998, no. 6, p. 785.

  19. Hofmann, H.-J. and Cimiraglia, B., Z. Chem., 1988, vol. 28, no.9, p. 326.

    Google Scholar 

  20. Adamczyk, M. and Mokrosz, M., Chem. Scripta, 1981, vol. 18, no.5, p. 237.

    Google Scholar 

  21. Mirek, J., Adamczyk, M., and Mokrosz, M., Synthesis, 1980, no. 4, p. 296.

  22. Freeman, F., Chem. Rev., 1980, vol. 80, no.4, p. 329.

    Article  Google Scholar 

  23. Sharanin, Yu.A., Promonenkov, V.K., and Litvinov, V.P., Itogi Nauki Tekh., Ser. Org. Khim., 1991, vol. 20, ch. 1.

  24. Korsakov, M.V., Belogorodskii, V.V., Korsakova, L.N., Belodedova, Zh.V., and Ivin, B.A., Zh. Org. Khim., 1983, vol. 19, no.3, p. 635.

    Google Scholar 

  25. Zil’berman, E.N., Reaktsii nitrilov (Reactions of Nitriles), Moscow: Khimiya, 1972.

    Google Scholar 

  26. US Patent 5 631 401, Ref. Zh. Khim., 1998, 22 O31 P.

  27. DE Patent Application 19518988, Ref. Zh. Khim., 1998, Ref. Zh. Khim., 1999, 3 O365 P.

  28. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12, p. S1.

  29. Marchalin, S., Ilavsky, D., Kovac, J., and Bruncko, M., Collect. Czech. Chem. Commun., 1990, vol. 55, no.3, p. 718.

    Google Scholar 

  30. Watkin, D.J., Prout, C.K., Carruthers, J.R., and Betteridge, P.W., Crystals, issue 10, Chemical Crystallography Laboratory, Oxford: Univ. of Oxford, 1996.

    Google Scholar 

  31. Frolova, N.G., Zav’yalova, V.K., and Litvinov, V.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1996, no. 4, p. 938.

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Authors and Affiliations

  1. Shevchenko National Pedagogical University, Lugansk, Ukraine

    V. D. Dyachenko

  2. Institute of Organic Chemistry, National Academy of Sciences, Kiev, Ukraine

    A. N. Chernega

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  1. V. D. Dyachenko
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  2. A. N. Chernega
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__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 6, 2005, pp. 1007–1016.

Original Russian Text Copyright © 2005 by Dyachenko, Chernega.

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Dyachenko, V.D., Chernega, A.N. Isobutyraldehyde in the Synthesis of Isopropyl-substituted 4H-Pyrans, 1,4-Dihydropyrano[2,3-c]pyrazole, 1,4-Dihydropyridines, and Cyclobutane. Russ J Gen Chem 75, 952–960 (2005). https://doi.org/10.1007/s11176-005-0351-6

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  • DOI: https://doi.org/10.1007/s11176-005-0351-6

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