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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

1H,4H-Piperazine-diium Dichlorosulfonate: Structure Elucidation and its Dual Solvent–Catalyst Activity for the Synthesis of New Dihydro-[1,2,4]triazolo[1,5-a]pyrimidine Scaffolds

Lia Zaharani A , Nader Ghaffari Khaligh https://orcid.org/0000-0001-9585-9253 A C , Taraneh Mihankhah B and Mohd Rafie Johan A
+ Author Affiliations
- Author Affiliations

A Nanotechnology and Catalysis Research Center, Institute of Postgraduate Studies, University of Malaya, 50603 Kuala Lumpur, Malaysia.

B Environmental Research Laboratory, Department of Water and Environmental Engineering, School of Civil Engineering, Iran University of Science and Technology, 16765-163, Tehran, Iran.

C Corresponding author. Email: ngkhaligh@gmail.com

Australian Journal of Chemistry 73(11) 1118-1124 https://doi.org/10.1071/CH20022
Submitted: 18 January 2020  Accepted: 1 April 2020   Published: 23 June 2020

Abstract

A new ionic liquid containing a 1H,4H-piperazine-diium ring and chlorosulfonate as a 1,4-dicationic core and counter ion, respectively, was designed and synthesised. The structure elucidation of this ionic liquid was conducted by 1D and 2D NMR, FT-IR, Raman, and mass spectrum analysis. The physical properties of this ionic liquid were determined and reported. Furthermore, the dual solvent–catalyst activity of piperazine-1,4-diium dichlorosulfonate was investigated for the synthesis of new dihydro[1,2,4]triazolo[1,5-a]pyrimidines through a one-pot three-component reaction. The ionic liquid was retrieved and reused several times without reducing its catalytic efficiency.


References

[1]  T. Welton, Biophys. Rev. 2018, 10, 691.
         | Crossref | GoogleScholarGoogle Scholar | 29700779PubMed |

[2]  N. G. Khaligh, L. S. Teng, O. C. Ling, M. R. Johan, J. J. Ching, J. Mol. Liq. 2019, 278, 19.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  N. G. Khaligh, T. Mihankhah, M. R. Johan, J. J. Ching, Phosphorus, Sulfur, Silicon Relat. Elem. 2019, 194, 866.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  N. G. Khaligh, K. F. Chong, T. Mihankhah, S. Titinchi, M. R. Johan, J. J. Ching, Aust. J. Chem. 2018, 71, 566.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  N. G. Khaligh, T. Mihankhah, M. R. Johan, Polycycl. Arom. Comp. 2019,
         | Crossref | GoogleScholarGoogle Scholar |

[6]  K. Oukoloff, B. Lucero, K. R. Francisco, K. R. Brunden, C. Ballatore, Eur. J. Med. Chem. 2019, 165, 332.
         | Crossref | GoogleScholarGoogle Scholar | 30703745PubMed |

[7]  N. Zhang, S. A. Kaloustian, T. Nguyen, J. Afragola, R. Hernandez, J. Lucas, J. Gibbons, C. Beyer, J. Med. Chem. 2007, 50, 319.
         | Crossref | GoogleScholarGoogle Scholar | 17228873PubMed |

[8]  G. M. Esteban-Parra, J. M. Méndez-Arriaga, A. Rodríguez-Diéguez, M. Quirós, J. M. Salas, M. Sánchez-Moreno, J. Inorg. Biochem. 2019, 201, 110810.
         | Crossref | GoogleScholarGoogle Scholar | 31493678PubMed |

[9]  R. H. Abd El-Aleam, R. F. George, G. S. Hassan, H. M. Abdel-Rahman, Bioorg. Chem. 2020, 94, 103411.
         | Crossref | GoogleScholarGoogle Scholar | 31711767PubMed |

[10]  Y. A. H. Mostafa, M. A. Hussein, A. A. Radwan, A. E. N. Kfafy, Arch. Pharm. Res. 2008, 31, 279.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  H. Wang, M. Lee, Z. Peng, B. Blazquez, E. Lastochkin, M. Kumarasiri, R. Bouley, M. Chang, S. Mobashery, J. Med. Chem. 2015, 58, 4194.
         | Crossref | GoogleScholarGoogle Scholar | 25923368PubMed |

[12]  F. Yang, L. Z. Yu, P. C. Diao, X. E. Jian, M. F. Zhou, C. S. Jiang, W. W. You, W. F. Ma, P. L. Zhao, Bioorg. Chem. 2019, 92, 103260.
         | Crossref | GoogleScholarGoogle Scholar | 31525523PubMed |

[13]  B. Huang, C. Li, W. Chen, T. Liu, M. Yu, L. Fu, Y. Sun, H. Liu, E. D. Clercq, C. Pannecouque, J. Balzarini, P. Zhan, X. Liu, Eur. J. Med. Chem. 2015, 92, 754.
         | Crossref | GoogleScholarGoogle Scholar | 25626145PubMed |

[14]  Q. Chen, X. L. Zhu, L. L. Jiang, Z. Ming, L. Guang, F. Yang, Eur. J. Med. Chem. 2008, 43, 595.
         | Crossref | GoogleScholarGoogle Scholar | 17618711PubMed |

[15]  G. Fischer, in Advanced Heterocyclic Chemistry (Ed. A. R. Katritzky) 2007, Vol. 95, pp. 143–219 (Academic Press: New York, NY).

[16]  M. Fizer, M. Slivka, Chem. Heterocycl. Compd. 2016, 52, 155.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  N. G. Khaligh, T. Mihankhah, M. R. Johan, J. Mol. Liq. 2019, 277, 794.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  W. W. Simons, Sadtler Handbook of Proton NMR Spectra (Index Included) 1978 (Sadtler Research Laboratories: Philadelphia, PA).

[19]  R. C. Paul, K. K. Paul, K. C. Malhotra, Aust. J. Chem. 1969, 22, 847.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  T. C. Waddington, F. Klanberg, J. Chem. Soc. 1960, 1960, 2339.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  R. A. Heacock, L. Marion, Can. J. Chem. 1956, 34, 1782.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  M. F. Erben, C. O. Della Ve’dova, R. Boese, H. Willner, C. Leibold, H. Oberhammer, Inorg. Chem. 2003, 42, 7297.
         | Crossref | GoogleScholarGoogle Scholar | 14577800PubMed |

[23]  R. J. Gillespie, E. A. Robinson, Can. J. Chem. 1962, 40, 644.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  E. Steger, L. C. Ciurea, A. Fudini, Z. Anorg. Allg. Chem. 1967, 350, 225.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  D. J. Stufkens, H. Gerding, Recl. Trav. Chim. Pays Bas 1970, 89, 417.
         | Crossref | GoogleScholarGoogle Scholar |