Summary.
A series of ureidopropenenitriles were synthesised by Knoevenagel condensation of ArCOCH2CN and HC(OEt)3 in presence of ureas in a one pot reaction. These ureidopropenenitriles were cyclised to 4-aryl-5-cyano-3-substituted pyrimidines (in acid) or to 4-amino-5-benzoylpyrimidines (in base) in 60–70% yields. The amine pyrimidine derivatives were further converted to substituted uracils by hydrolysis with isopentyl nitrite in DMF. Alkylation of uracils furnished 1,3-dimethyluracil derivatives with DMS in alkali. All new compounds were characterised by spectral and analytical methods.
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Jachak, M., Tantak, C., Toche, R. et al. A Convenient Route for the Synthesis of 4-Aryl- and 4-Aminopyrimidines. Monatshefte für Chemie 135, 1529–1538 (2004). https://doi.org/10.1007/s00706-004-0192-8
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DOI: https://doi.org/10.1007/s00706-004-0192-8