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Exploring the acidic catalytic role of differently structured deep eutectic solvents in the aza-Michael addition of amines to 2-vinylpiridine

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Abstract

The search for innovative and green reaction media is a prominent topic in the recent research in chemistry. Deep Eutectic Solvents (DESs) are currently gaining relevance in this field thanks to their unique properties in terms of their “greenness” as well as in terms of their catalytic properties. In this work we developed an efficient protocol for the conjugate aza-Michael addition of amines to 2-vinylpyridine using 14 differently structured acid DESs as both reaction media and catalysts, so preventing the use of other acid additives. The results are influenced by the acidity of the components of the DESs, showing the best results with weak acids in the DESs components, with isolated yields up to 86%. The aza-Michael reaction is a widely used synthetic route for the C–N bond formation in organic synthesis. In particular, the addition of amines to 2-vinylpyridine is used for the realization of pharmaceutically relevant compounds with anticancer, antiarrhythmic, and analgesic properties. Comparing the results with the ones observed in literature for the same reaction, this procedure revealed to be a convenient and efficient method for this relevant transformation.

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Authors and Affiliations

  1. Department of Chemistry, Biology and Biotechnology, University of Perugia, via Elce di Sotto 8, 06123, Perugia, Italy

    Marco Ballarotto, Federico Cappellini, Riccardo Maestri, Tiziana Del Giacco, Matteo Tiecco & Raimondo Germani

  2. Department of Pharmaceutical Sciences, University of Perugia, via del Liceo 1, 06123, Perugia, Italy

    Marco Ballarotto

  3. Department of Pharmacy, University of Chieti-Pescara “G. D’Annunzio”, via dei Vestini 31, 66100, Chieti, Italy

    Pietro Di Profio

Authors
  1. Marco Ballarotto
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  2. Federico Cappellini
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  3. Riccardo Maestri
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  4. Tiziana Del Giacco
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  5. Pietro Di Profio
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  6. Matteo Tiecco
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  7. Raimondo Germani
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Correspondence to Matteo Tiecco.

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Ballarotto, M., Cappellini, F., Maestri, R. et al. Exploring the acidic catalytic role of differently structured deep eutectic solvents in the aza-Michael addition of amines to 2-vinylpiridine. Monatsh Chem 151, 1387–1394 (2020). https://doi.org/10.1007/s00706-020-02660-z

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  • DOI: https://doi.org/10.1007/s00706-020-02660-z

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