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Synthesis, properties, and mass-spectrometric fragmentation of 2-thio derivatives of 3-arylquinazolin-4-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have studied the reactions of alkylation, oxidation, and hydrolysis of 3-aryl-2-thioxoquinazolin-4-ones. Alkylation in an alkaline medium occurs exclusively at the sulfur atom. Oxidation by hydrogen peroxide leads to formation of 3-arylquinazoline-2,4-diones. The latter are also obtained in base or acid hydrolysis of the synthesized S-alkyl derivatives. When 3-aryl-2-thioxoquinazolin-4-ones are reacted with iodine, we obtain the disulfides, while the reaction with chlorine in hydrochloric acid leads to 2-chloroquinazolin-4-ones. Studying the mass spectrometric behavior of the compounds obtained made it possible to observe in the gas phase ring-chain isomerization of the heterocyclic ring, and also S-N migration of the propargyl radical in molecular ions of the S-propargyl derivatives.

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References

  1. S. Johne and D. Groeger, Pharmazie, 25, 22 (1970).

    CAS  Google Scholar 

  2. S. Johne, Pharmazie, 36, 583 (1981).

    CAS  Google Scholar 

  3. J. B. Hynes and W. T. Ashton, J. Med. Chem., 18, 263 (1975).

    Article  CAS  Google Scholar 

  4. E. T. Elslager, P. Jacob, J. Johnson, and L. M. Werbel, J. Heterocycl. Chem., 17, 129 (1980).

    Article  CAS  Google Scholar 

  5. I. P. Tregubenko, B. V. Golomolzin, I. Ya. Postovskii, V. I. Filyakova, and É. A. Tarakhtii, in: Organic Synthesis and Biological Activity [in Russian], Sverdlovsk (1978), p. 3.

  6. B. V. Golomolzin, I. P. Tregubenko, E. A. Tarakhtii, L. N. Rasina, and O. N. Tikhonova, in: Organic Synthesis and Biological Activity [in Russian], Sverdlovsk (1978), p. 14.

  7. M. S. Mevada, G. R. Dave, and C. C. Amin, J. Sci. Ind. Res., 20, 299 (1961); Chem. Abstr., 56, 2448.

    Google Scholar 

  8. L. Gattermann, Ber., 32, 1136 (1899).

    CAS  Google Scholar 

  9. R. O. Roblin and J. W. Clapp, J. Am. Chem. Soc., 72, 4890 (1950).

    Article  CAS  Google Scholar 

  10. W. Knobloch and K. Rintelen, Arch. Pharm., 291, 180 (1958).

    Article  CAS  Google Scholar 

  11. K. M. Krivozheiko and A. V. El’tsov, Zh. Org. Khim., 4, 1114 (1968).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Ural State Technical University, Ekaterinburg, 620002, Russia

    Yu. A. Azev, B. V. Golomolzin & Yu. G. Yatluk

  2. Bremen University, Germany, D28334

    T. Dyulcks

  3. Institute of Ecology and Evolution Problems, Russian Academy of Sciences, Moscow, 117071

    N. A. Klyuev

Authors
  1. Yu. A. Azev
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  2. B. V. Golomolzin
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  3. T. Dyulcks
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  4. N. A. Klyuev
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  5. Yu. G. Yatluk
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 440–446, March, 2007.

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Azev, Y.A., Golomolzin, B.V., Dyulcks, T. et al. Synthesis, properties, and mass-spectrometric fragmentation of 2-thio derivatives of 3-arylquinazolin-4-ones. Chem Heterocycl Compd 43, 356–361 (2007). https://doi.org/10.1007/s10593-007-0052-7

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  • DOI: https://doi.org/10.1007/s10593-007-0052-7

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