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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 10, pp 934–939 | Cite as

Green Synthesis and Z/E-Isomerization of Novel Coumarin Enamines Induced by Organic Solvents

  • Abolfazl Olyaei
  • Soheila Javarsineh
  • Mahdieh Sadeghpour
Article
  • 29 Downloads

An efficient and straightforward synthesis of novel (Z/E)-3-[(heteroarylamino)methylidene]chromane-2,4-dione derivatives via a one-pot three-component condensation of 4-hydroxycoumarin, triethyl orthoformate, and heteroaryl amines in the presence of guanidinium chloride as organocatalyst under solvent-free conditions is described. Investigation of spectroscopy data indicated that coumarin enamines exist in the ketoenamine tautomeric form and undergo Z/E-isomerization in respect to the C=C bond in CDCl3 and DMSO-d6 at room temperature. Furthermore, intramolecular hydrogen bonds have been observed in the synthesized compounds. Also, 1H NMR spectra indicated that E-ketoenamines are the major isomers. High to excellent yields, short reaction times, simple workup, and very easy purification of products by non-chromatographic methods are advantages of this synthetic procedure.

Keywords

chromane 4-hydroxycoumarin ketoenamine triethyl orthoformate Z/E-isomerization 

Notes

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

Supplementary material

10593_2018_2376_MOESM1_ESM.pdf (2.5 mb)
ESM 1 (PDF 2526 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Abolfazl Olyaei
    • 1
  • Soheila Javarsineh
    • 1
  • Mahdieh Sadeghpour
    • 2
  1. 1.Department of ChemistryPayame Noor UniversityTehranIran
  2. 2.Department of Chemistry, Takestan BranchIslamic Azad UniversityTakestanIran

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