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4-(N,N-Dialkylthiocarbamoylthio)-5-nitropyrimidines as new potential nitric oxide donors

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Abstract

On heating at pH 6.86, 4-(N,N-dialkylthiocarbamoylthio)-5-nitropyrimidines are transformed into dithiolopyrimidines, which are either oxidized to bis(4-dialkylthiocarbamoylpyrimidin-5-yl) disulfides or converted into 4,6-diamino-5-nitropyrimidine derivatives with carbon disulfide elimination. The direction of the reaction is determined by the nature of a substituent in position 2 of pyrimidine and the bulk of the thiocarbamate substituent. Mechanistic schemes for these processes were proposed.

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Authors and Affiliations

  1. State Scientific Center of Antibiotics, 3a ul. Nagatinskaya, 117105, Moscow, Russian Federation

    O. B. Ryabova, E. Yu. Khmel’nitskaya, V. A. Makarov, L. M. Alekseeva, N. B. Grigor’ev & V. G. Granik

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  1. O. B. Ryabova
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  2. E. Yu. Khmel’nitskaya
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  3. V. A. Makarov
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  4. L. M. Alekseeva
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  5. N. B. Grigor’ev
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  6. V. G. Granik
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2777–2783, December, 2005.

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Ryabova, O.B., Khmel’nitskaya, E.Y., Makarov, V.A. et al. 4-(N,N-Dialkylthiocarbamoylthio)-5-nitropyrimidines as new potential nitric oxide donors. Russ Chem Bull 54, 2873–2879 (2005). https://doi.org/10.1007/s11172-006-0203-5

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  • DOI: https://doi.org/10.1007/s11172-006-0203-5

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