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

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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.

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Science, South Tehran Branch, Islamic Azad University, Tehran, Iran

    Vahid Beigi-Somar & Seyed Saied Homami

  2. Center for Catalysis Research and Innovation, BAHERENERGY Institute of Technology, P.O. Box 13487-55613, Tehran, Iran

    Majid Ghazanfarpour-Darjani

  3. Department of Polymer and Textile Engineering, South Tehran Branch, Islamic Azad University, Tehran, Iran

    Amirhossein Monzavi

Authors
  1. Vahid Beigi-Somar
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  2. Seyed Saied Homami
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  3. Majid Ghazanfarpour-Darjani
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  4. Amirhossein Monzavi
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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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  • DOI: https://doi.org/10.1007/s00706-020-02548-y

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