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Acylamino-Substituted Vinylphosphonium Salts in Syntheses of Derivatives of Nitrogen Heterocycles

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Abstract

The results of 25-year studies of acylamino-substituted vinylphosphonium salts (AVPOSs), accessible and unique reagents for various heterocyclizations, are summarized. The main synthetic routes to AVPOSs, their transformations into various heterylphosphonium salts, and dephosphorylation of these salts are considered in detail. Particular attention is given to interpretation of the reactivity of mesomeric phosphonium ylide-betaines of the heterocyclic series, derived from AVPOSs. The advantages of these reagents in preparative syntheses of phosphorus-free functional derivatives of azoles and azines are demonstrated. Based on these data, peculiar features of AVPOSs are revealed, and a general concept of phosphonium syntheses of heterocyclic compounds is substantiated.

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Authors and Affiliations

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

    B. S. Drach, V. S. Brovarets & O. B. Smolii

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  1. B. S. Drach
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  2. V. S. Brovarets
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  3. O. B. Smolii
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Drach, B.S., Brovarets, V.S. & Smolii, O.B. Acylamino-Substituted Vinylphosphonium Salts in Syntheses of Derivatives of Nitrogen Heterocycles. Russian Journal of General Chemistry 72, 1661–1687 (2002). https://doi.org/10.1023/A:1023320608504

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