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

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作者
O. B. Smolii
L. V. Muzychka
A. N. Chernega
B. S. Drach
机构
[1] National Academy of Sciences of Ukraine,Institute of Bioorganic Chemistry and Petrochemistry
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关键词
Iodide; Vinyl; Pyrimidine; Amidine; Benzamidine;
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摘要
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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页码:527 / 532
页数:5
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