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Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation

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Abstract

The palladium-catalyzed carbonylation of iodoferrocene was investigated in the presence of 2-aminopyrimidine derivatives as nucleophiles. 2-Amino-4-hydroxy-6-methylpyrimidine was found to act both as an O- and an N-nucleophile, leading to an ester and an amide derivative, respectively. Together with other spectroscopic methods, the structure of both products was proved by X-ray crystallography. 2-(Ferrocenoylamino)-4-chloro-6-alkylpyrimidines were obtained during carbonylation of iodoferrocene and 2-amino-4-chloro-6-alkylpyrimidines. The formation of a dimeric product via two subsequent carbonylation steps was also observed. The products may have practical importance as electrochemically detectable biosensors or building blocks for supramolecular assemblies.

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Acknowledgments

The authors thank the Hungarian National Science Foundation (OTKA K105632) and COST Action CM1005 for financial support. Mrs B. Norberg is acknowledged for technical assistance during X-ray diffraction analysis.

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Authors and Affiliations

  1. Department of Organic Chemistry, Institute of Chemistry, University of Veszprém, Egyetem u. 10, P.O. Box 158, 8200, Veszprem, Hungary

    Csaba Fehér & Rita Skoda-Földes

  2. Ruđer Bošković Insitute, Bijenička c. 54, P.O. Box 180, 10002, Zagreb, Croatia

    Ivan Habuš

  3. Department of Chemistry, Université de Namur, Rue de Bruxelles 61, 5000, Namur, Belgium

    Johan Wouters

Authors
  1. Csaba Fehér
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  2. Ivan Habuš
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  3. Johan Wouters
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  4. Rita Skoda-Földes
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Correspondence to Rita Skoda-Földes.

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Fehér, C., Habuš, I., Wouters, J. et al. Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation. Monatsh Chem 145, 1981–1986 (2014). https://doi.org/10.1007/s00706-014-1299-1

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  • DOI: https://doi.org/10.1007/s00706-014-1299-1

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