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Microwave-assisted synthesis of 2,5-diarylthiazolo[5,4-d]thiazoles from benzaldehydes and dithiooxamide

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Abstract

One-pot condensation of dithiooxamide with aromatic aldehydes and subsequent oxidation of intermediate 2,5-dihydro[1,3]thiazolo[5,4-d][1,3]thiazoles with selenium dioxide afforded 2,6-diaryl[1,3]thiazolo-[5,4-d][1,3]thiazoles which were characterized by 1H and 13C NMR, IR, and X-ray diffraction data.

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References

  1. Bevk, D., Marin, L., Lutsen, L., Vanderzande, D., and Maes, W., RSC Adv., 2013, vol. 3, p. 11 418.

    Article  CAS  Google Scholar 

  2. Smirnova, N.G., Zavarzin, I.V., and Krayushkin, M.M., Chem. Heterocycl. Compd., 2006, vol. 42, no. 2, p. 144.

    Article  CAS  Google Scholar 

  3. Yokokawa, F., Sameshima, H., and Shioiri, T., Tetrahedron Lett., 2001, vol. 42, p. 4171.

    Article  CAS  Google Scholar 

  4. Hughes, R.A., Thompson, S.P., Alcaraz, L., and Moody, C.J., J. Am. Chem. Soc., 2005, vol. 127, p. 15 644.

    Article  CAS  Google Scholar 

  5. Jung, I.H., Yu, J., Jeong, E., Kim, J., Kwon, S., Kong, H., Lee, K., Woo, H.Y., and Shim, H.-K., Chem. Eur. J., 2010, vol. 16, p. 3743.

    Article  CAS  Google Scholar 

  6. Osaka, I., Sauvé, G., Zhang, R., Kowalewski, T., and McCullough, R.D., Adv. Mater., 2007, vol. 19, p. 4160.

    Article  CAS  Google Scholar 

  7. Craft, A., Grimsdale, A.C., and Holmes, A.B., Angew. Chem., Int. Ed., 1998, vol. 37, p. 402.

    Article  Google Scholar 

  8. Ando, S., Nishida, J., Tada, H., Inoue, Y., Tokito, S., and Yamashita, Y., J. Am. Chem. Soc., 2005, vol. 127, p. 5336.

    Article  CAS  Google Scholar 

  9. Osaka, I., Zhang, R., Sauvé, G., Smilgies, D.-M., Kowalewski, T., and McCullough, R.D., J. Am. Chem. Soc., 2009, vol. 131, p. 2521.

    Article  CAS  Google Scholar 

  10. Knighton, R.C., Hallett, A.J., Kariuki, B.M., and Pope, S.J.A., Tetrahedron Lett., 2010, vol. 51, p. 5419.

    Article  CAS  Google Scholar 

  11. Pinto, M.R., Takahata, Y., and Atvars, T.D.Z., J. Photochem. Photobiol. A: Chem., 2001, vol. 143, p. 119.

    Article  CAS  Google Scholar 

  12. Anthony, J.E., Angew. Chem., Int. Ed., 2008, vol. 47, p. 452.

    Article  CAS  Google Scholar 

  13. Peng, Q., Peng, J.-B., Kang, E.T., Neoh, K.G., and Cao, Y., Macromolecules, 2005, vol. 38, p. 7292.

    Article  CAS  Google Scholar 

  14. Zampese, J.A., Keene, F.R., and Steel, P.J., J. Chem. Soc., Dalton Trans., 2004, p. 4124.

    Google Scholar 

  15. Yousif, Y.Z. and Al-Namdani, A.J., Liq. Cryst., 1993, vol. 15, no. 4, p. 451.

    Article  CAS  Google Scholar 

  16. Johnson, J.R. and Ketcham, R., J. Am. Chem. Soc., 1960, vol. 82, p. 2719.

    Article  CAS  Google Scholar 

  17. Ando, S., Kumaki, D., Nishida, J., Tada, H., Inoue, Y., Tokito, S., and Yamashita, Y.S., J. Mater. Chem., 2007, vol. 17, p. 553.

    Article  CAS  Google Scholar 

  18. Johnson, J.R., Rotenberg, D.H., and Ketcham, R., J. Am. Chem. Soc., 1970, vol. 92, p. 4046.

    Article  CAS  Google Scholar 

  19. Falcao, E.H.L., Naraso, Feller, R.K., Wu, G., Wudl, F., and Cheetham, A.K., Inorg. Chem., 2008, vol. 47, no. 18, p. 8336.

    Article  CAS  Google Scholar 

  20. Mamada, M., Nishida, J., Kumaki, D., Tokito, S., and Yamashita, Y., Chem. Mater., 2007, vol. 19, p. 5404.

    Article  CAS  Google Scholar 

  21. Seybold, G. and Eilingsfeld, H., Justus Liebigs Ann. Chem., 1979, no. 9, p. 1271.

    Google Scholar 

  22. Roetling, T., Kibbel, H., Kochmann, W., and Naumann, K., DD Patent no. 210 457, 1984.

  23. Dessi, A., Calamante, M., Mordini, A., Zani, L., Taddei, M., and Reginato, G., RSC Adv., 2014, vol. 4, p. 1322.

    Article  CAS  Google Scholar 

  24. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    L. K. Papernaya, A. A. Shatrova, I. V. Sterkhova, G. G. Levkovskaya & I. B. Rozentsveig

Authors
  1. L. K. Papernaya
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  2. A. A. Shatrova
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  3. I. V. Sterkhova
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  4. G. G. Levkovskaya
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  5. I. B. Rozentsveig
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Correspondence to L. K. Papernaya.

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Original Russian Text © L.K. Papernaya, A.A. Shatrova, I.V. Sterkhova, G.G. Levkovskaya, I.B. Rozentsveig, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 389–393.

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Papernaya, L.K., Shatrova, A.A., Sterkhova, I.V. et al. Microwave-assisted synthesis of 2,5-diarylthiazolo[5,4-d]thiazoles from benzaldehydes and dithiooxamide. Russ J Org Chem 51, 373–377 (2015). https://doi.org/10.1134/S1070428015030148

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  • DOI: https://doi.org/10.1134/S1070428015030148

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