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Formation of epoxychromeno[4,3-c]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]-2H-chromen-2-one and furfurylamine

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Abstract

An intramolecular Diels–Alder mediated reaction of (2E)-3-(4-chloro-2-methylene-2H-chromen-3-yl)-1-phenyl-2-propen-1-one, which was obtained in situ from the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde and Wittig reagent, with furfurylamine leads to fused epoxychromeno[4,3-c]isoquinolines. Reaction performed in one-pot condition and only one diastereomer was obtained. In this method, the key step for the formation of the final product is IMDA reaction.

Graphic abstract

A series of fused epoxychromeno[4,3-c]isoquinoline compounds containing chromene skeleton have been synthesized through the cyclization strategy, from 4-chloro-2-oxo-2H-chromene-3-carbaldehyde, Wittig reagent, and furfurylamine. The reactions were carried out under reflux condition in DCM/toluene.

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Acknowledgements

We gratefully acknowledge the support of this work by the Tarbiat Modares University Research Council.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Abdolali Alizadeh, Kaveh Amir Ashjei Asalemi & Behnaz Farajpour

  2. Chemistry and Chemical Engineering Research Center of Iran (CCERCI), Pajohesh Blvd, 17th Km of Tehran-Karaj Highway, Tehran, 1496813151, Iran

    Mohammad Reza Halvagar

Authors
  1. Abdolali Alizadeh
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  2. Kaveh Amir Ashjei Asalemi
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  3. Behnaz Farajpour
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  4. Mohammad Reza Halvagar
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Correspondence to Abdolali Alizadeh.

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Alizadeh, A., Amir Ashjei Asalemi, K., Farajpour, B. et al. Formation of epoxychromeno[4,3-c]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]-2H-chromen-2-one and furfurylamine. J IRAN CHEM SOC 17, 3393–3399 (2020). https://doi.org/10.1007/s13738-020-01999-8

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