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A catalytic multicomponent protocol to dihydropyridine-3-carboxylate from terminal alkynes, isocyanates, and malonates

Abstract

A domino catalytic reaction between terminal alkynes, isocyanates, and malonates has been developed. Copper acetylides attack on isocyanates to form a propargylic amide species which further reacted with malonates by the action of t-BuOLi to form dihydropyridine-3-carboxylates. The regioselectivity of the reaction has been examined with unsymmetrical malonate. The procedure is easy to implement, has a broad scope and allows the construction of the scaffolds by creating three covalent bonds in one pot.

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Acknowledgements

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

Author information

Correspondence to Seyed Saied Homami.

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Beigi-Somar, V., Homami, S.S., Ghazanfarpour-Darjani, M. et al. A catalytic multicomponent protocol to dihydropyridine-3-carboxylate from terminal alkynes, isocyanates, and malonates. Monatsh Chem 151, 231–241 (2020). https://doi.org/10.1007/s00706-020-02548-y

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Keywords

  • Terminal alkyne
  • Isocyanate
  • Malonate
  • Cyclization
  • Copper catalysis