Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

  • Damiano Rocchi, Juan F. González, Jorge Gómez-Carpintero, Víctor González-Ruiz, M. Antonia Martín, Vellaisamy Sridharan, J. Carlos Menéndez
  • ACS Combinatorial Science, October 2018, American Chemical Society (ACS)
  • DOI: 10.1021/acscombsci.8b00137

What is it about?

The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m- terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

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The following have contributed to this page: M. Antonia Martín