Unusual heterocyclization of chalcone podands with 3-amino-1,2,4-triazole |
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Authors: | Ovchinnikova I G Valova M S Matochkina E G Kodess M I Tumashov A A Slepukhin P A Fedorova O V Rusinov G L Charushin V N |
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Institution: | 1.I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation ; |
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Abstract: | A new type of intramolecular cyclization of 1,5-bis2-(E-3-oxo-3-phenylprop-1-enyl)-phenoxy]-3-oxapentane with 3-aminotriazole promoted by potassium ions was discovered. A cascade
mechanism for the formation of crownophane with 4,7-dihydro1,2,4]triazolo1,5-a]-pyrimidine fragment was suggested. Effects of oligooxyethylene fragment of the chalcone podand and acid-base catalysis on
the selectivity of the cyclocondensation processes and degree of oxidation of triazolopyrimidine fragments were studied. The
product structures were confirmed by IR, 1H and 13C NMR spectroscopy and X-ray diffraction study. |
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