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A copper-catalyzed reaction between terminal alkynes, acetylenic esters, and oxiranes: efficient synthesis of 2H-pyran-4-carboxylate

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Abstract

A catalytic reaction between terminal alkynes, acetylenic esters, and oxiranes has been described. This domino transformation serves as a useful sequential and one-pot method for the synthesis of 2H-pyran-4-carboxylate skeletons from the readily available starting materials. In situ-generated copper acetylides treated initially with oxiranes in the presence of copper catalysts and tetrabutylphosphonium salts, followed by addition of propiolates after 60 min to form synthetically important heterocycles.

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Acknowledgements

We wish to thank for a grant from Islamic Azad University, South Tehran Branch.

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Correspondence to Mohammadreza Manafi or Majid Ghazanfarpour-Darjani.

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Jahanshad, M., Manafi, M., Mousavi-Safavi, S.M. et al. A copper-catalyzed reaction between terminal alkynes, acetylenic esters, and oxiranes: efficient synthesis of 2H-pyran-4-carboxylate. Monatsh Chem 151, 113–122 (2020) doi:10.1007/s00706-019-02526-z

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Keywords

  • Domino reaction
  • Three-membered heterocycle
  • Copper catalysis
  • Acetylenic ester
  • Cyclization