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Efficient pseudo five-component synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives promoted by a novel ionic liquid catalyst

  • Zahra Abshirini and Abdolkarim Zare EMAIL logo
Published/Copyright: March 14, 2018
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 73 Issue 3-4

Abstract

In this research, initial production and characterization of a novel Brønsted-acidic ionic liquid, namely, N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2), has been described (characterization was achieved using Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass and thermal gravimetric spectra). Thereafter, utilization of [TMEDSA][HSO4]2 as a highly effectual catalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives through the one-pot pseudo five-component reaction of phenylhydrazine (2 eq.) with ethyl acetoacetate (2 eq.) and arylaldehydes (1 eq.) in relatively mild conditions, has been reported.

Keywords: 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H- pyrazol-5-ol); Brønsted-acidic ionic liquid; multicomponent reaction; N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2); pseudo five-component reaction

Acknowledgment

The authors acknowledge the support of this work by the Research Council of Payame Noor University.

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Supplemental Material:

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2017-0179).

Received: 2017-10-14
Accepted: 2017-12-1
Published Online: 2018-3-14
Published in Print: 2018-4-25

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Does Lewis basicity correlate with catalytic performance in zerovalent group 8 complexes?
  4. Crystal structure and luminescence properties of a new dinuclear bismuth(III) coordination polymer containing three types of ligands
  5. Syntheses, structures, and catalytic properties of two arene-ruthenium(II) complexes bearing N-(2-pyridinyl)aminodiphenylphosphine sulfide ligands
  6. Synthesis, characterization, anticancer and antimicrobial study of arene ruthenium(II) complexes with 1,2,4-triazole ligands containing an α-diimine moiety
  7. Green synthesis of α-aminophosphonates using ZnO nanoparticles as an efficient catalyst
  8. Nano-NiZr4(PO4)6 as a superior catalyst for the synthesis of propargylamines under ultrasound irradiation
  9. Efficient pseudo five-component synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives promoted by a novel ionic liquid catalyst
  10. Hydrothermal synthesis and crystal structure of a bisupporting Keggin-polyoxometalate hybrid compound decorated with a copper(II) complex unit
  11. Synthesis, crystal structure, luminescence and electrochemical properties of a Salamo-type trinuclear cobalt(II) complex
  12. New cholic acid analogs: synthesis and 17β-hydroxydehydrogenase (17β-HSD) inhibition activity
  13. Synthesis, vibrational spectra and single-crystal structure determination of lithium tricyanomethanide Li[C(CN)3]
  14. Silber(I)-cyanid-Komplexe mit Aminen und Azaaromaten
  15. The alkaline earth-palladium-germanides Sr3Pd4Ge4 and BaPdGe
  16. Equiatomic rare earth rhodium plumbides RERhPb (RE=Y, La–Nd, Sm, Gd–Lu) with ZrNiAl-type structure
  17. Notes
  18. Synthesis and crystal structure of [azido-bis(cis-1,2-diaminocyclohexane)copper(II)] chloride trihydrate
  19. A Co(II) complex from a pyridylamide ligand: synthesis and structural characterization
https://doi.org/10.1515/znb-2017-0179
Keywords for this article
4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H- pyrazol-5-ol); Brønsted-acidic ionic liquid; multicomponent reaction; N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate ([TMEDSA][HSO4]2); pseudo five-component reaction

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Does Lewis basicity correlate with catalytic performance in zerovalent group 8 complexes?
  4. Crystal structure and luminescence properties of a new dinuclear bismuth(III) coordination polymer containing three types of ligands
  5. Syntheses, structures, and catalytic properties of two arene-ruthenium(II) complexes bearing N-(2-pyridinyl)aminodiphenylphosphine sulfide ligands
  6. Synthesis, characterization, anticancer and antimicrobial study of arene ruthenium(II) complexes with 1,2,4-triazole ligands containing an α-diimine moiety
  7. Green synthesis of α-aminophosphonates using ZnO nanoparticles as an efficient catalyst
  8. Nano-NiZr4(PO4)6 as a superior catalyst for the synthesis of propargylamines under ultrasound irradiation
  9. Efficient pseudo five-component synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives promoted by a novel ionic liquid catalyst
  10. Hydrothermal synthesis and crystal structure of a bisupporting Keggin-polyoxometalate hybrid compound decorated with a copper(II) complex unit
  11. Synthesis, crystal structure, luminescence and electrochemical properties of a Salamo-type trinuclear cobalt(II) complex
  12. New cholic acid analogs: synthesis and 17β-hydroxydehydrogenase (17β-HSD) inhibition activity
  13. Synthesis, vibrational spectra and single-crystal structure determination of lithium tricyanomethanide Li[C(CN)3]
  14. Silber(I)-cyanid-Komplexe mit Aminen und Azaaromaten
  15. The alkaline earth-palladium-germanides Sr3Pd4Ge4 and BaPdGe
  16. Equiatomic rare earth rhodium plumbides RERhPb (RE=Y, La–Nd, Sm, Gd–Lu) with ZrNiAl-type structure
  17. Notes
  18. Synthesis and crystal structure of [azido-bis(cis-1,2-diaminocyclohexane)copper(II)] chloride trihydrate
  19. A Co(II) complex from a pyridylamide ligand: synthesis and structural characterization
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