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Regioselectivity of cyclization of 1-(6-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)-4-arylthiosemicarbazides by treating with methyl iodide and dicyclohexylcarbodiimide

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Abstract

1-(6-Methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)-4-arylthiosemicarbazides treated with methyl iodide in the presence of sodium acetate in ethanol convert into 6-methyl-3-arylamino[1,2,4]-triazolo[4,3-b][1,2,4]triazin-7(1H)-ones. In reaction with dicyclohexylcarbodiimide 6-methyl-3-arylamino[1,2,4]triazolo[3,4-c][1,2,4]triazin-5(1H)-ones were obtained which at heating in alcohol solution in the presence of sodium acetate or at 262–272°C underwent the Dimroth rearrangement to give 3-methyl-7-arylamino[1,2,4]triazolo[5,1-c][1,2,4]-triazin-4(8H)-ones.

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References

  1. Vas’kevich, R.I., Savitskii, P.V., Zborovskii, Yu.L., Staninets, V.I., Rusanov, E.B., and Chernega, A.N., Zh. Org. Khim., 2006, vol. 42, p. 1417.

    Google Scholar 

  2. Vas’kevich, R.I., Savitskii, P.V., Zborovskii, Yu.L., Staninets, V.I., Turov, A.V., and Chernega, A.N., Zh. Org. Khim., 2006, vol. 42, p. 1411.

    Google Scholar 

  3. Savitskii, P.V., Vas’kevich, R.I., Zborovskii, Yu.L., Staninets, V.I., But, S.A., and Chernega, A.N., Zh. Org. Khim., 2008, vol. 44, p. 407.

    Google Scholar 

  4. Bishop, B.C., Marley, H., Preston, P.N., and Wright, S.H.B., J. Chem. Soc., Perkin, Trans. 1, 1999, p. 1527

  5. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Tailor, R. J. Chem. Soc., Perkin, Trans. 2, 1987, p. 1.

  6. Sheldric, G.M., SHELXS97. Program for the Solution of Crystal Structure, University of Göttingen, Germany, 1997.

    Google Scholar 

  7. Sheldric, G.M., SHELXL97. Program for the Refi nement of Srystal Structures, University of Göttingen, Germany, 1997.

    Google Scholar 

  8. Dornow, A., Abele, W., and Menzel, H., Chem. Ber., 1964, vol. 97, p. 2179.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 0209, Ukraine

    R. I. Vas’kevich, P. V. Savitskii, E. B. Rusanov & V. I. Staninets

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  1. R. I. Vas’kevich
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  2. P. V. Savitskii
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  3. E. B. Rusanov
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  4. V. I. Staninets
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Correspondence to R. I. Vas’kevich.

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Original Russian Text © R.I. Vas’kevich, P.V. Savitskii, E.B. Rusanov, V.I. Staninets, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 11, pp. 1675–1679.

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Vas’kevich, R.I., Savitskii, P.V., Rusanov, E.B. et al. Regioselectivity of cyclization of 1-(6-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)-4-arylthiosemicarbazides by treating with methyl iodide and dicyclohexylcarbodiimide. Russ J Org Chem 46, 1682–1686 (2010). https://doi.org/10.1134/S1070428010110138

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  • DOI: https://doi.org/10.1134/S1070428010110138

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