Startseite Naturwissenschaften 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
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

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 und Abdolkarim Zare EMAIL logo
Veröffentlicht/Copyright: 14. März 2018
Veröffentlichen auch Sie bei De Gruyter Brill

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.

Acknowledgment

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

References

[1] M. A. Waseem, Shireen, K. Ansari, F. Ibad, A. Ibad, J. Singh, I. R. Siddiqui, Tetrahedron Lett.2017, 58, 4169.10.1016/j.tetlet.2017.09.039Suche in Google Scholar

[2] H. R. Safaei, M. Shekouhy, V. Shafiee, M. Davoodi, J. Mol. Liq.2013, 180, 139.10.1016/j.molliq.2013.01.013Suche in Google Scholar

[3] J. Lunagariya, A. Dhar, R. L. Vekariya, RSC Adv.2017, 7, 5412.10.1039/C6RA26722JSuche in Google Scholar

[4] F. Abbasi, N. Azizi, M. Abdoli-Senejani, J. Iran. Chem. Soc.2017, 14, 2097.10.1007/s13738-017-1146-5Suche in Google Scholar

[5] A. A. Marzouk, A. A. Abdelhamid, S. K. Mohamed, J. Simpson, Z. Naturforsch.2017, 72b, 23.10.1515/znb-2016-0121Suche in Google Scholar

[6] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, M. Kruger, J. Org. Chem.2012, 77, 3640.10.1021/jo300137wSuche in Google Scholar PubMed

[7] A. Zare, Z. Nasouri, J. Mol. Liq.2016, 216, 364.10.1016/j.molliq.2016.01.056Suche in Google Scholar

[8] A. Zare, T. Yousofi, A. R. Moosavi-Zare, RSC Adv.2012, 2, 7988.10.1039/c2ra20679jSuche in Google Scholar

[9] A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal.2017, 7, 233.Suche in Google Scholar

[10] A. Gupta, R. Kaur, D. Singh, K. K. Kapoor, Tetrahedron Lett.2017, 58, 26, 2583.10.1016/j.tetlet.2017.05.067Suche in Google Scholar

[11] A. R. Moosavi-Zare, M. A. Zolfigol, S. Farahmand, A. Zare, A. R. Pourali, R. Ayazi-Nasrabadi, Synlett2014, 25, 193.10.1055/s-0033-1340088Suche in Google Scholar

[12] A. Rabiei, S. Abdolmohammadi, F. Shafaei, Z. Naturforsch.2017, 72b, 241.10.1515/znb-2016-0219Suche in Google Scholar

[13] M. Gökçe, S. Utku, E. Küpeli, Eur. J. Med. Chem.2009, 44, 3760.10.1016/j.ejmech.2009.04.048Suche in Google Scholar

[14] Y. Liu, G. He, C. Kai, Y. Li, H. Zhu, J. Heterocycl. Chem.2012, 49, 1370.10.1002/jhet.1045Suche in Google Scholar

[15] P. Manojkumar, T. K. Ravi, S. Gopalakrishnan, Eur. J. Med. Chem.2009, 44, 4690.10.1016/j.ejmech.2009.07.004Suche in Google Scholar

[16] N. Das, A. Verma, P. K. Shrivastava, S. K. Shrivastava, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.2008, 47B, 1555.Suche in Google Scholar

[17] K. R. Kim, K. Ju-Lee, K. Ji-Sun, N. Zaesung, R. K. Hyoung, G. C. Hyae, Eur. J. Pharmacol.2005, 528, 37.10.1016/j.ejphar.2005.10.027Suche in Google Scholar

[18] K. Sujatha, G. Shanthi, N. P. Selvam, S. Manoharan, P. T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett.2009, 19, 4501.10.1016/j.bmcl.2009.02.113Suche in Google Scholar

[19] M. F. Brana, A. Gradillas, A. G. Ovalles, B. López, N. Acero, F. Llinares, D. M. Mingarro, Bioorg. Med. Chem.2006, 14, 9.10.1016/j.bmc.2005.09.059Suche in Google Scholar

[20] D. Castagnolo, A. D. Logu, M. Radi, B. Bechi, F. Manetti, M. Magnani, S. Supino, R. Meleddu, L. Chisu, M. Botta, Bioorg. Med. Chem.2008, 16, 8587.10.1016/j.bmc.2008.08.016Suche in Google Scholar

[21] C. Pettinari, F. Marchetti, R. Pettinari, A. Drozdov, S. Troyanov, A. I. Voloshin, J. Chem. Soc., Dalton Trans.2002, 1409.10.1039/b108058jSuche in Google Scholar

[22] M. Londershausen, Pestic. Sci.1996, 48, 269.10.1002/(SICI)1096-9063(199612)48:4<269::AID-PS478>3.0.CO;2-BSuche in Google Scholar

[23] A. Khazaei, F. Abbasi, A. R. Moosavi-Zare, New J. Chem.2014, 38, 5287.10.1039/C4NJ01079ESuche in Google Scholar

[24] A. R. Moosavi-Zare, M. A. Zolfigol, E. Noroozizadeh, O. Khaledian, B. Shirmardi Shaghasemi, Res. Chem. Intermed.2016, 42, 4759.10.1007/s11164-015-2317-6Suche in Google Scholar

[25] D. Banerjee, R. Karmakar, U. Kayal, G. Maiti, Synth. Commun.2017, 47, 1006.10.1080/00397911.2017.1298134Suche in Google Scholar

[26] S. Tayebi, K. Niknam, Iran. J. Catal.2012, 2, 69.Suche in Google Scholar

[27] C. Yang, P.-Z. Liu, D.-Z. Xu, ChemistrySelect2017, 2, 1232.10.1002/slct.201601801Suche in Google Scholar

[28] A. Hassankhani, J. Mex. Chem. Soc.2015, 59, 1.Suche in Google Scholar

[29] A. Hasaninejed, M. Rasekhi Kazerooni, A. Zare, ACS Sustain. Chem. Eng.2013, 1, 679.10.1021/sc400081cSuche in Google Scholar

[30] F. Shirini, M. Seddighi, M. Mazloumi, M. Makhsous, M. Abedini, J. Mol. Liq.2015, 208, 291.10.1016/j.molliq.2015.04.027Suche in Google Scholar


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

Artikel in diesem Heft

  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
Heruntergeladen am 10.3.2026 von https://www.degruyterbrill.com/document/doi/10.1515/znb-2017-0179/html
Button zum nach oben scrollen