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Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives

  • Abolfazl OlyaeiEmail author
  • Reyhaneh Mohammad Ebrahimi
  • Alireza Adl
  • Mahdieh Sadeghpour
Article
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A facile, convenient, and efficient synthesis of new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives has been accomplished via one-pot three-component reaction of 4-aminocoumarin, 1,3-dicarbonyl compounds (dimedone and Meldrum's acid), and substituted aromatic aldehydes in H2O or EtOH under reflux conditions using 10 mol % of guanidine hydrochloride as organocatalyst. Formation of products proceeds through tandem Knoevenagel and Michael reactions, followed by concomitant cyclization and dehydration or decarboxylation. A wide range of aromatic aldehydes were tolerated by the developed protocol. The advantages of this environmentally friendly synthetic approach are short reaction times, high atom economy, operational simplicity, application of readily available catalyst, z high yields of products, simple workup procedure, and possibility to purify products by recrystallization.

Keywords

4-aminocoumarin chromeno[4,3-b]pyridine chromeno[4,3-b]quinoline guanidine hydrochloride 

Notes

The authors thank Research Council of the Payame Noor University for financial support.

Supplementary material

10593_2019_2585_MOESM1_ESM.pdf (3.8 mb)
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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Abolfazl Olyaei
    • 1
    Email author
  • Reyhaneh Mohammad Ebrahimi
    • 1
  • Alireza Adl
    • 1
  • Mahdieh Sadeghpour
    • 2
  1. 1.Department of ChemistryPayame Noor UniversityTehranIran
  2. 2.Department of Chemistry, Takestan BranchIslamic Azad UniversityTakestanIran

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