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Fused pyrimidine systems: XVI. Electrophilic intramolecular cyclization of 2-(alkenylsulfanyl)pteridin-4(3H)-ones

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Abstract

2-[Allyl(but-3-en-1-yl, pent-4-en-1-yl)sulfanyl]pteridin-4(3Н)-ones at heating in polyphosphoric acid undergo an intramolecular cyclization affording respectively 9-methyl-8,9-dihydro-5H-[1,3]thiazolo[3,2-a] pteridin-5-one and 10-methyl(ethyl)-9,10-dihydro-5Н,8Н-[1,3]thiazino[3,2-a]pteridin-5-ones of angular structure. The cyclization of 2-(alkenylsulfanyl)pteridin-4(3Н)-ones under the action of iodine or arylsulfenyl chlorides afforded iodo(arylsulfanyl) derivatives of angularly fuzed thiazolo- and thiazinopteridines.

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References

  1. Dyachenko, I.V., Vas’kevich, A.I., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 858.

    Article  CAS  Google Scholar 

  2. Pfleider, W., J. Heterocycl. Chem., 1992, vol. 29, p. 583.

    Article  Google Scholar 

  3. Milstien, S., Kapatos, G., Levine, R.A., and Shane, B, Chemistry and Biology of Pteridines and Folates, Proceedings of the 12th International Symposium on Pteridines and Folates, National Institutes of Health, Bethesda, Maryland, 2002, XXIII, 677 p.

    Google Scholar 

  4. Ahmed, S.A., Elghandour, A.H., and Elgeny, H.S., Pharm. Chem., 2014, vol. 6, p. 194.

    Google Scholar 

  5. Shaifullah, A.Z.M.S., Shibata, Y., Morita, M., Kaya, K., and Hiratani, K., J. Heterocycl. Chem., 2001, vol. 38, p. 1173.

    Article  Google Scholar 

  6. Southon, I.W. and Pfleider, W., Chem. Ber., 1978, vol. 111, p. 971.

    Article  CAS  Google Scholar 

  7. Falch, E., Acta Chem. Scand., 1977, vol. 31B, p. 167.

    Article  Google Scholar 

  8. Vas’kevich, R.I., Khripak, S.M., Staninets, V.I., Zborovskii, Yu.L., and Chernega, A.N., Zh. Org. Khim., 2000, vol. 36, p. 1091.

    Google Scholar 

  9. Vas’kevich, R.I., Khripak, S.M., Staninets, V.I., Zborovskii, Yu.L., Nesterenko, A.M., and Pirozhenko, V.V., Ukr. Khim. Zh., 2000, vol. 66, p. 47.

    Google Scholar 

  10. Bentya, A.V., Vas’kevich, R.I., Bol’but, A.V., Vovk, M.V., Staninets, V.I., Turov, A.V., and Rusanov, E.B., Russ. J. Org., 2008, vol. 44, p. 1362.

    Article  CAS  Google Scholar 

  11. Bentya, A.V., Vas’kevich, R.I., and Staninets, V.I., Ukr. Khim. Zh., 2008, vol. 74, p. 94.

    CAS  Google Scholar 

  12. Dyachenko, I.V., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 263.

    Article  CAS  Google Scholar 

  13. Dyachenko, I.V., Vas’kevich, A.I., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 858.

    Article  CAS  Google Scholar 

  14. Prem, M.S., Chauhan, P.M.S., Cristina, J.A., Martins, C.J.A., and Horwell, D.C., Bioorg. Med. Chem., 2005, vol. 13, p. 3513.

    Article  Google Scholar 

  15. Sheldrick, M., Acta Cryst., 2008, Sect. A, vol. 64, p. 112.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya ul. 5, Kiev, 02094, Ukraine

    I. V. Dyachenko, R. I. Vas’kevich & M. V. Vovk

  2. R&D Enterprise “Enamin,”, Kiev, Ukraine

    R. I. Vas’kevich

  3. National Technical University of Ukraine, “Kiev Polytechnic Institute,”, Kiev, Ukraine

    A. I. Vas’kevich

  4. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Kharkiv, Ukraine

    S. V. Shishkina

  5. Karazin Kharkiv National University, Kharkiv, Ukraine

    S. V. Shishkina

Authors
  1. I. V. Dyachenko
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  2. R. I. Vas’kevich
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  3. A. I. Vas’kevich
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  4. S. V. Shishkina
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  5. M. V. Vovk
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Corresponding author

Correspondence to A. I. Vas’kevich.

Additional information

Original Russian Text © I.V. Dyachenko, R.I. Vas’kevich, A.I. Vas’kevich, S.V. Shishkina, M.V. Vovk, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 5, pp. 755–762.

For communication XV, see [1].

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Dyachenko, I.V., Vas’kevich, R.I., Vas’kevich, A.I. et al. Fused pyrimidine systems: XVI. Electrophilic intramolecular cyclization of 2-(alkenylsulfanyl)pteridin-4(3H)-ones. Russ J Org Chem 52, 745–752 (2016). https://doi.org/10.1134/S1070428016050225

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  • DOI: https://doi.org/10.1134/S1070428016050225

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