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Research on Chemical Intermediates

, Volume 41, Issue 11, pp 8483–8497 | Cite as

Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives

  • Farhad ShiriniEmail author
  • Mohaddeseh Safarpoor Nikoo Langarudi
  • Mohadeseh Seddighi
  • Omid Goli Jolodar
Article

Abstract

1,8-Dioxo-octahydro-xanthenes are easily prepared via the condensation of aldehydes with 1,3-cyclohexadione and/or dimedone using N-sulfonated DABCO as a new and efficient catalyst. This reagent is also efficiently able to catalyze the condensation of aldehydes with barbituric acid leading to 5-arylmethylene-pyrimidine-2,4,6-triones. The structure of the products was characterized by their IR, 1H NMR, and 13C NMR spectroscopy. The present methodology offers several advantages such as ease of preparation and handling of the catalyst, high yields, simple and green procedure, low cost, short reaction times, easy work-up, and preformation of the reaction in the absence of solvent or in water as a green solvent.

Keywords

N-sulfonated DABCO {[DABCO](SO3H)2(Cl)2Solvent-free conditions 5-Arylmethylene-pyrimidine-2,4,6-trione 1,8-Dioxo-octahydro-xanthene Aldehyde Barbituric acid 

Notes

Acknowledgments

The authors are thankful to the University of Guilan Research Council for the partial support of this work.

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Farhad Shirini
    • 1
    Email author
  • Mohaddeseh Safarpoor Nikoo Langarudi
    • 1
  • Mohadeseh Seddighi
    • 1
  • Omid Goli Jolodar
    • 1
  1. 1.Department of Chemistry, College of ScienceUniversity of GuilanRashtIran

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