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Reactions of alkyl 2-benzylidene-2-polyfluoroacylacetates with N,N-dinucleophiles

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Abstract

Alkyl 2-benzylidene-2-polyfluoroacylacetates react with urea and thiourea to yield 5-ethoxycarbonyl-4-fluoroalkyl-4-hydroxy-6-phenylhexahydropyrimidin-2-ones and -2-thiones and with guanidine sulfate to form 2-amino-5-ethoxycarbonyl-4-fluoroalkyl-6-phenyl-1,6-dihydropyrimidines and 3,6-diethoxycarbonyl-2,7-difluoroalkyl-4,5-diphenyl-4,5-dihydro-1H-pyrido[1,2-a]pyrimidines, and they react with phenylhydrazine to afford 4-alkoxycarbonyl-3-fluoroalkyl-3-hydroxy-1,5-diphenylpyrazolidines. Hydrazine hydrate catalyzes the formation of 3,5-diethoxycarbonyl-2,6-difluoroalkyl-2,6-dihydroxy-4-phenyltetrahydropyrans. When treated with anhydrous hydrazine and o-phenylenediamine, these esters cleave to form the products of condensation of fluoroacyl ester and benzaldehyde with diamines.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620219 Ekaterinburg, Russian Federation, Russia

    M. V. Pryadeina, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin & O. N. Chupakhin

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  1. M. V. Pryadeina
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  2. Ya. V. Burgart
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  3. M. I. Kodess
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  4. V. I. Saloutin
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  5. O. N. Chupakhin
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Pryadeina, M.V., Burgart, Y.V., Kodess, M.I. et al. Reactions of alkyl 2-benzylidene-2-polyfluoroacylacetates with N,N-dinucleophiles. Russian Chemical Bulletin 53, 1261–1266 (2004). https://doi.org/10.1023/B:RUCB.0000042284.03940.41

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  • DOI: https://doi.org/10.1023/B:RUCB.0000042284.03940.41

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