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Paper | Special issue | Vol 82, No. 1, 2010, pp.593-601
Published online, 16th June, 2010
DOI: 10.3987/COM-10-S(E)29
Direct Oxidative Conversion of Aldehydes into 2-Substituted 1,4,5,6-Tetrahydropyrimidines Using Molecular Iodine or 1,3-Diiodo-5,5-dimethylhydantoin

Shogo Takahashi and Hideo Togo*

*Graduate School of Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Various aromatic and aliphatic aldehydes were efficiently converted into the corresponding 1,4,5,6-tetrahydro-2-arylpyrimidines and 1,4,5,6-tetrahydro-2-alkylpyrimidines in good yields by the reaction with 1,3-propanediamine in the presence of molecular iodine•K2CO3 or 1,3-diiodo-5,5-dimethylhydantoin. Those 1,4,5,6-tetrahydropyrimidines were oxidized to the corresponding 2-aryl- and 2-alkylpyrimidines in moderate yields using MnO2.