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Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines

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Abstract

Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.

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Acknowledgements

We are thankful to the Center of Excellence (Chemistry), Research Council and Office of Graduate Studies of the University of Isfahan for their financial support.

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Author notes

  1. Asadallah Farhadi

    Present address: Faculty of Petroleum Engineering, Petroleum University of Technology of Ahwaz, 44471-61981, Ahwaz, Iran

Authors and Affiliations

  1. Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, 81746-73441, Isfahan, Iran

    Hamid Reza Memarian & Nazanin Jafarpour

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  1. Hamid Reza Memarian
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  2. Nazanin Jafarpour
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  3. Asadallah Farhadi
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Correspondence to Hamid Reza Memarian.

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Memarian, H.R., Jafarpour, N. & Farhadi, A. Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines. Monatsh Chem 143, 277–281 (2012). https://doi.org/10.1007/s00706-011-0573-8

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  • DOI: https://doi.org/10.1007/s00706-011-0573-8

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