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Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
62
Issue
41
Identifiers
DOI: 10.1016/j.tet.2006.07.063
Keywords
  • Oxidation
  • Pyrimidines
  • 3
  • 4-Dihydropyrimidin-2(1H)-Ones
  • Ceric Ammonium Nitrate

Abstract

Abstract Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1 H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 °C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1 H)-one-5-carboxylate was obtained by performing the reaction with NaHCO 3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1 H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions.

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