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Catalytic synthesis of 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-ones) and 3,3,6,6-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones

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Abstract

Condensation of substituted benzaldehydes of vanillin series with dimedone in methanol solution in the presence of catalytic quantities of triethylamine afforded 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-ones. By catalytic cyclization of the latter in boiling benzene in the presence of sulfo cation exchanger FIBAN K-1 as catalyst 3,3,6,6-trimethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones were synthesized.

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References

  1. Hunnur, R.K., Sunilkumar, B., Kumar, P.S., Srinivasulu, N., Udupi, R.H., and Himabindu, V., Khim. Geterotsikl. Soedin., 2008, p. 196; Bhattacharya, A.K., Rana, K.C., Mujahid, M., Sehar, I., and Saxena, A.K., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 5590; Okuma, K., Nojima, A., Matsunaga, N., and Shioji, K., Org. Lett., 2009, vol. 11, p. 169; Giri, R., Goodell, J.R., Xing, C., Benoit, A., Kaur, H., Hiasa, H., and Ferguson, D.M., Bioorg. Med. Chem., 2010, vol. 18, p. 1456; Xu, X.B., Xu, X.L., Li, H., Xie, X., and Li, Y., Org. Lett., 2010, vol. 12, p. 100; Btsb, E., Hillringhaus, T., Klussmann, M., and Nitsch, J., Org. Biomol. Chem., 2011, vol. 9, p. 1744; Rahmatpour, A., Monatsh. Chem. Chem. Month., 2011, vol. 142, p. 1259; Nandi, M., Mondal, J., Sarkar, K., Yamauchi, Y., and Bhaumik, A., Chem. Commun., 2011, vol. 47, p. 6677; Moghadam, M., Tangestaninejad, S., Mirkhani, V., Mohammadpoor-Baltork, I., and Moosavifar, M., C. r., 2011, vol. 14, p. 489; Lu, C., Dubrovskiy, A.V., Larock, and R.C., Tetrahedron Lett., 2012, p. 53, p. 2202; Prasad, D. and Nath, M., Catal. Sci. Technol., 2012, vol. 2, p. 93; Allameh, S., Davoodnia, A., and Khojastehnezhad, A., Chin. Chem. Lett., 2012, vol. 23, p. 17.

    Google Scholar 

  2. Horning, E.C. and Horning, M.J., J. Org. Chem., 1946, vol. 11, p. 95; Jones, G., Org. Reactions., 1967, vol. 15, p. 204; Fieser, L. F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley-Intersci., 1972; Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley-Intersci., 1982, vol..2.

    Article  CAS  Google Scholar 

  3. Soldatov, V.S., Elinson, I.S., Shunkevich, A.A., Pawlowski, L., Wasag, H., Environmental, Sci. Research. Chemistry for the Protection of Environment, New York: Plenum Press, 1996, vol. 51, p. 55; Egiazarov, Yu.G., Potapova, L.L., Radkevich, V.Z., Soldatov, V.S., Shunkevich, A.A., and Cherches, B.Kh., Khimiya v interesakh, ustoichivogo razvitiya (Chemistry for Stable Development), 2001, vol. 3, p. 417.

    Book  Google Scholar 

  4. Desiraju, G.R. and Steiner, T., The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford: University Press, 2001, p. 480.

    Book  Google Scholar 

  5. Dikusar, E.A., Kozlov, N.G., Potkin, V.I., Yuvchenko, A.P., and Tlegenov, R.T., Zameshchennye benzaldehydey vanillinovogo ryada v organicheskom sinteze: poluchenie, primenenie, biologicheskaya aktivnost’ (Substituted Benzaldehydes of Vanillin Series in Organic Synthesis: Preparation, Application, Biological Activity), Minsk: Pravo i Ekonomika, 2011, p. 446; Dikusar, E.A., Potkin, V.I., and Kozlov, N.G., Benzaldehydey vanillinovogo ryada. Sintez, proizvodnykh, primenenie i biologicheskaya aktivnost’ (Benzaldehydes of Vanillin Series. Synthesis of Derivatives, Application, and Biological Activity), Saarbr’cken, Germany: LAP, LAMBERT, Academic, Publishing, GmbH, &, Co. KG, 2012, p. 612.

    Google Scholar 

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Correspondence to E. A. Dikusar.

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Original English Text © E.A. Dikusar, V.I. Potkin, N.G. Kozlov, A.S. Pavlyuchenkova, M.Yu. Murashova, S.K. Petkevich, A.V. Kletskov, A.P. Polikarpov, M.M. Ogorodnikova, R.M. Zolotar’, O.P. Chepik, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 2, pp. 243–251.

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Dikusar, E.A., Potkin, V.I., Kozlov, N.G. et al. Catalytic synthesis of 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-ones) and 3,3,6,6-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-diones. Russ J Org Chem 49, 233–242 (2013). https://doi.org/10.1134/S1070428013020103

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  • DOI: https://doi.org/10.1134/S1070428013020103

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