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Research on Chemical Intermediates

, Volume 44, Issue 10, pp 6253–6266 | Cite as

A novel dicationic ionic liquid as a highly effectual and dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones

  • Navid Irannejad-Gheshlaghchaei
  • Abdolkarim ZareEmail author
  • Seyed Sajad SajadikhahEmail author
  • Alireza Banaei
Article

Abstract

A novel dicationic ionic liquid, N,N,N′,N′-tetramethyl-N,N′-bis(sulfo)ethane-1,2-diaminium mesylate [TMBSED][OMs]2), has been produced, and identified by analysis of its 1H NMR, 13C NMR, FT-IR, mass and thermal gravimetric data. Thereafter, it has been utilized as a highly effectual, homogeneous and dual-functional catalyst to promote the multi-component reaction of ethyl acetoacetate, hydroxylamine hydrochloride and arylaldehydes under solvent-free conditions for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones. Due to the dual-functionality of [TMBSED][OMs]2 (possessing acidic and basic sites), and also having two sites of each, it was a highly effective and general catalyst for the synthesis. Moreover, a plausible and attractive mechanism based on the dual-functionality of the catalyst has been proposed.

Graphical Abstract

Keywords

N,N,N′,N′-Tetramethyl-N,N′-bis(sulfo)ethane-1,2-diaminium mesylate ([TMBSED][OMs]2Dicationic ionic liquid Dual-functional catalyst 3-Methyl-4-arylmethylene-isoxazole-5(4H)-one Multi-component reaction Solvent-free 

Notes

Acknowledgement

We thank the Research Council of Payame Noor University for providing the necessary research facilities and the financial support of this work.

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© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran

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