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Cyclocondensation of [1-Cyano-2-(methylsulfanyl)vinyl]triphenylphosphonium Iodide with Amidine Nucleophiles

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Abstract

The substituted vinylphosphonium salt (E)-MeSCH=C(CN)P+Ph3I− readily cyclizes under the action of benzamidine and 3-amino-s-triazole, but it does not enter cyclocondensation with 2-aminopyridine. The structure of the cyclization product with 3-amino-s-triazole was confirmed by its transformation to 7-imino-6-(triphenylphosphoranylidene)-6,7-dihydro-s-triazolo[1,5]pyrimidine which was identified by X-ray diffraction. This stabilized ylide and its analogs proved useful starting materials for regioselective syntheses of 2-R-4-alkyl-4,7-dihydro-s-triazolo[1,5-a]pyrimidin-7-ones.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    O. B. Smolii, L. V. Muzychka, A. N. Chernega & B. S. Drach

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  1. O. B. Smolii
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  2. L. V. Muzychka
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  3. A. N. Chernega
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  4. B. S. Drach
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 565–570.

Original Russian Text Copyright © 2005 by Smolii, Muzychka, Chernega, Drach.

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Smolii, O.B., Muzychka, L.V., Chernega, A.N. et al. Cyclocondensation of [1-Cyano-2-(methylsulfanyl)vinyl]triphenylphosphonium Iodide with Amidine Nucleophiles. Russ J Gen Chem 75, 527–532 (2005). https://doi.org/10.1007/s11176-005-0266-2

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  • DOI: https://doi.org/10.1007/s11176-005-0266-2

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