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Light-induced dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones

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Abstract

UV light irradiation of Biginelli 3,4-dihydropyrimidin-2(1H)-ones in chloroform in an argon atmosphere leads to dehydrogenation of these compounds to their corresponding pyrimidin-2(1H)-ones in excellent yields. Irradiation in the same solvent under an oxygen atmosphere generates, in addition, various hitherto unidentified products. A light-induced electron transfer from the substrate to the solvent is proposed as the initial event, supported by the detection of dichloromethane and hydrogen chloride in the photolysate.

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Acknowledgments

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

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Authors and Affiliations

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

    Hamid Reza Memarian & Asadollah Farhadi

Authors
  1. Hamid Reza Memarian
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  2. Asadollah Farhadi
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Correspondence to Hamid Reza Memarian.

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Memarian, H.R., Farhadi, A. Light-induced dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones. Monatsh Chem 140, 1217–1220 (2009). https://doi.org/10.1007/s00706-009-0156-0

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  • DOI: https://doi.org/10.1007/s00706-009-0156-0

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