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Monatshefte für Chemie - Chemical Monthly

, Volume 147, Issue 10, pp 1779–1787 | Cite as

Tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst for one-pot synthesis of Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives

  • Mahsa Yarhosseini
  • Shahrzad JavanshirEmail author
  • Mohammad G. Dekamin
  • Mohammad Farhadnia
Original Paper

Abstract

A green, convenient, and environment-friendly approach for the synthesis of biologically active Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives in the presence of tetraethylammonium 2-(carbamoyl)benzoate, as an effective bifunctional metal-free catalyst, has been developed via a one-pot multicomponent reaction of various aldehydes, ethyl acetoacetate or cyclic 1,3-dicarbonyl compounds, and ammonium acetate in EtOH under reflux conditions. The proposed methodology is capable of providing the desired products in good to excellent yields and short reaction time with straightforward work-up and a low-cost procedure.

Graphical abstract

Keywords

Tetraethylammonium 2-(carbamoyl)benzoate Multicomponent reaction 1,4-Dihydropyridine Polyhydroquinoline Green chemistry 

Notes

Acknowledgments

We are grateful for the financial support from The Research Council of Iran University of Science and Technology (IUST), Tehran, Iran.

Supplementary material

706_2016_1666_MOESM1_ESM.docx (4.2 mb)
Supplementary material 1 (DOCX 4310 kb)

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Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  • Mahsa Yarhosseini
    • 1
  • Shahrzad Javanshir
    • 1
    Email author
  • Mohammad G. Dekamin
    • 1
  • Mohammad Farhadnia
    • 1
  1. 1.Department of ChemistryIran University of Science and TechnologyTehranIran

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