Fully Substituted Dihydropyrimidines, Pentasubstituted 2-Aryldihydropyrimidines Synthesized by Palladium-Catalyzed/Copper-Mediated Cross-Coupling Reaction

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公開日
2023-02-08
資源種別
journal article
DOI
  • 10.1055/a-2030-7730
公開者
Georg Thieme Verlag KG

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説明

<jats:title>Abstract</jats:title><jats:p>Dihydropyrimidines (DPs) show a wide range of biological activities suitable for medicinal applications. Among DP derivatives, 2-aryl-DPs have been reported to display remarkable pharmacological properties. In this work, a method of synthesizing hitherto unavailable fully substituted pentasubstituted 2-aryl-DPs as tautomeric mixture is described using a Pd(PPh3)4-catalyzed/CuBr-mediated 2-arylation reaction. The reaction using aryltributylstannanes with various substituents such as MeO, Me, Ph, CF3, CO2Me, and NO2 groups efficiently afforded the corresponding 2-aryl-DPs in high yields. Heteroaryltributylstannanes having 2-thienyl, 3-thienyl, or 2-pyridinyl groups were also suitable for the reaction. Regarding the substituents at the 4-, 5-, and 6-positions of DPs, the reactions of DPs bearing substituents such as Me, n-C3H7, n-C5H11, -(CH2)5-, phenyl, and fluorenylidene groups proceeded smoothly to give the desired products. The synthetic method was also applied to a 2-thioxo-DP to give the 2-aryl-DP. Therefore, the reaction will help expand DP-based molecular diversity, which may impact biological and pharmacological studies.</jats:p>

収録刊行物

  • Synthesis

    Synthesis 55 (13), 1996-2004, 2023-02-08

    Georg Thieme Verlag KG

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