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Reaction of unsymmetrical α,β-unsaturated ketones with thiobarbituric acid

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Abstract

Carbocyclization of unsymmetrical 1,5-diarylpenta-1,4-dien-3-ones with thiobarbituric acid afforded previously unknown 7,11-diaryl-3-thioxo-2,4-diazaspiro[5.5]undecane-1,5,9-triones with high regio- and stereoselectivity. The same spiro compounds were also synthesized by three-component condensation of thiobarbituric acid with the corresponding aromatic aldehydes and 4-arylbut-3-en-2-ones.

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References

  1. Vatsadze, S.Z., Golikov, A.G., Kriven’ko, A.P., and Zyk, N.V., Usp. Khim., 2008, vol. 77, p. 707.

    Article  Google Scholar 

  2. Boukamcha, N., Gharbi, R., Martin, M.-T., Chiaroni, A., Mighri, Z., and Khemiss, F.A., Tetrahedron, 1999, vol. 55, p. 449.

    Article  CAS  Google Scholar 

  3. Muthasamy, S., Krishnamurthi, J., Babu, S.A., and Suresh, E., J. Org. Chem., 2007, vol. 72, p. 1252.

    Article  Google Scholar 

  4. Padmavathi, V., Reddy, T.V.R., Reddy, K.A., and Reddy, D.B., J. Heterocycl. Chem., 2003, vol. 40, p. 149.

    Article  CAS  Google Scholar 

  5. Gulai, T.V., Morozova, A.A., and Golikov, A.G., Russ. J. Org. Chem., 2011, vol. 47, p. 1690.

    Article  CAS  Google Scholar 

  6. Behera, R.K., Behera, A.K., Pradhan, R., Pati, A., and Patra, M., Synth. Commun., 2008, vol. 36, p. 3729.

    Article  Google Scholar 

  7. Sazonov, A.A., Frantsuzov, A.A., and Klochkova, I.N., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2005, vol. 48, no. 3, p. 127.

    CAS  Google Scholar 

  8. Lorand, T., Kocsis, B., Emody, L., and Sohar, P., Eur. J. Med. Chem., 1999, vol. 34, p. 1009.

    Article  CAS  Google Scholar 

  9. Al-Arab, M.M., Al-Saleh, F.S., and Mayoof, S.M., J. Heterocycl. Chem., 1998, vol. 35, p. 1473.

    Article  CAS  Google Scholar 

  10. Klochkova, I.N., Anis’kov, A.A., and Shchekina, M.P., Khim. Geterotsikl. Soedin., 2011, p. 1425.

    Google Scholar 

  11. Rosamila, A.E., Giarrusso, M.A., Scott, J.L., and Strauss, C.R., Green Chem., 2006, p. 1042.

    Google Scholar 

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Correspondence to A. A. Anis’kov.

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Original Russian Text © I.N. Klochkova, A.A. Anis’kov, M.P. Shchekina, S.V. Chuvaikina, K.A. Andreev, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1359–1362.

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Klochkova, I.N., Anis’kov, A.A., Shchekina, M.P. et al. Reaction of unsymmetrical α,β-unsaturated ketones with thiobarbituric acid. Russ J Org Chem 49, 1344–1347 (2013). https://doi.org/10.1134/S1070428013090169

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  • DOI: https://doi.org/10.1134/S1070428013090169

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