Journal of the Iranian Chemical Society

, Volume 16, Issue 1, pp 151–160 | Cite as

Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction

  • Ali KeivanlooEmail author
  • Mahsa Fakharian
  • Mohammad Reza Nabid
  • Amir Hossein Amin
Original Paper


A novel, simple, and efficient protocol is described for the synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via the one-pot reaction of phenol or 2-naphthol derivatives, propargyl bromide, and N-alkyl-3-chloroquinoxaline-2-amines in the presence of palladium catalyst. This one-pot reaction is carried out in the absence of any copper salt at room temperature. The reaction product is dependent on the nature of the base used. The use of morpholine, as the base, affords the final cyclized product, and triethylamine only gives the coupling product.

Graphical abstract


Sonogashira coupling Palladium-catalyzed reaction Copper-free Propargyl bromide Pyrrolo[2,3-b]quinoxalines 



We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

Supplementary material

13738_2018_1492_MOESM1_ESM.docx (11.3 mb)
Supplementary material 1 (DOCX 11521 KB)


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Copyright information

© Iranian Chemical Society 2018
corrected publication September/2018

Authors and Affiliations

  1. 1.Faculty of ChemistryShahrood University of TechnologyShahroodIran
  2. 2.Department of Chemistry and Petroleum Faculty of SciencesShahid Beheshti UniversityTehranIran

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