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A four-component Pfitzinger reaction: synthesis of 2-pyronylquinolin-4-carbamides

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Abstract

A one-pot route was developed for efficient synthesis of novel 2-substituted quinolin-4-carboxamides via a four-component sequential reaction between isatins, ammonium acetate, triethyl orthoacetate, and 4-hydroxycoumarin or 4-hydroxy-6-methyl-2H-pyran-2-one. This protocol is an extension of Pfitzinger’s quinoline synthesis and involves an unprecedented in situ iminoacetylation of 2H-pyrone ring at the 3-position followed sequentially by an isatin-ring-opening and a rearranged cyclization reaction. The products are covalently bound couples of quinolin-4-carboxamides and 4-hydroxycoumarin/4-hydroxy-6-methyl-2H-pyran-2-one heterocyclic nuclei with structures that are supported by their NMR, IR, and mass spectral data.

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Acknowledgements

We gratefully acknowledge the financial support from the Research Councils of Islamic Azad University, North branch, and the University of Guilan.

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Authors and Affiliations

  1. Chemistry Department, Islamic Azad University, Tehran-North Branch, Tehran, Iran

    Sorayya Yaghoubi Kalurazi & Shahram Moradi

  2. Chemistry Department, University of Guilan, Rasht, P.O. Box 41335-1914, Iran

    Kurosh Rad-Moghadam

Authors
  1. Sorayya Yaghoubi Kalurazi
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  2. Kurosh Rad-Moghadam
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  3. Shahram Moradi
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Correspondence to Kurosh Rad-Moghadam.

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Kalurazi, S.Y., Rad-Moghadam, K. & Moradi, S. A four-component Pfitzinger reaction: synthesis of 2-pyronylquinolin-4-carbamides. Res Chem Intermed 43, 4401–4411 (2017). https://doi.org/10.1007/s11164-017-2885-8

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