The structure elucidation of new ionic liquid and its application for the synthesis of a series of novel triazolo[1,5-a]pyrimidine scaffolds

被引:10
作者
Shahnavaz, Zohreh [1 ]
Khaligh, Nader Ghaffari [1 ]
Zaharani, Lia [1 ]
Johan, Mohd Rafie [1 ]
Hamizi, Nor Aliya [1 ]
机构
[1] Univ Malaya, Nanotechnol & Catalysis Res Ctr, Inst Postgrad Studies, 3rd Floor,Block A, Kuala Lumpur 50603, Malaysia
关键词
Ionic liquid; Raman spectroscopy; Homogeneous catalysis; Heterocycles; Waste prevention; CHLOROSULFONIC ACID; INFRARED SPECTRA; SULFONATION; CATALYST; AGENTS;
D O I
10.1016/j.molstruc.2020.128592
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the present study, the chemical structure of 4,4'-trimethylene-N,N'-dipiperidinium chlorosulfonate is elucidated by 1D NMR, and 2D NMR, FTIR, Raman analyses, and Mass spectra. It was indicated that the chlorosulfonic acid could not act as a sulfonating agent in the reaction with secondary amines like TMDP due to due more steric hindrance of the sulfur atom by chlorine and oxygen atoms. Raman and FTIR spectra are demonstrated as two high-value optical techniques to the elucidation and identification of chemical structures that confirmed C3(v) symmetry for chlorosulfonate anion in the ionic liquid. Then, the solvent-catalyst activity of ionic liquid was demonstrated in the one-pot synthesis of a series of novel triazolo-pyrimidines under mild conditions. The ionic liquid was retrieved and reused several times without reducing its catalytic efficiency. (C) 2020 Elsevier B.V. All rights reserved.
引用
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页数:7
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共 35 条
  • [1] Synthesis of 1,2,4-triazolo[1,5-a]pyrimidine derivatives: Antimicrobial activity, DNA Gyrase inhibition and molecular docking
    Abd El-Aleam, Rehab H.
    George, Riham F.
    Hassan, Ghaneya S.
    Abdel-Rahman, Hamdy M.
    [J]. BIOORGANIC CHEMISTRY, 2020, 94
  • [2] Bakker BH, 1999, EUR J ORG CHEM, V1999, P91
  • [3] 3-Methylpiperidinium ionic liquids
    Belhocine, Tayeb
    Forsyth, Stewart A.
    Gunaratne, H. Q. Nimal
    Nieuwenhuyzen, Mark
    Nockemann, Peter
    Puga, Alberto V.
    Seddon, Kenneth R.
    Srinivasan, Geetha
    Whiston, Keith
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2015, 17 (16) : 10398 - 10416
  • [4] Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives
    Chen, Qiong
    Zhu, Xiao-Lei
    Jiang, Li-Li
    Liu, Zu-Ming
    Yang, Guang-Fu
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) : 595 - 603
  • [5] PREPARATION AND INFRARED SPECTRA OF ALKALI AND ALKALINE EARTH METAL CHLOROSULFATES
    CIRUNA, JA
    ROBINSON, EA
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (10): : 1715 - &
  • [6] High antiparasitic activity of silver complexes of 5,7-dimethyl-1,2,4-triazolo [1,5 α] pyrimidine
    Esteban-Parra, Gines M.
    Mendez-Arriaga, Jose M.
    Rodriguez-Dieguez, Antonio
    Quiros, Miguel
    Salas, Juan M.
    Sanchez-Moreno, Manuel
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2019, 201
  • [7] Recent Progress in 1,2,4-Triazolo[1,5-a]pyrimidine Chemistry
    Fischer, Gunther
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 95, 2008, 95 : 143 - 219
  • [8] Synthesis of [1,2,4]triazolo[1,5-a]pyrimidine (microreview)
    Fizer, Maksym
    Slivka, Mikhailo
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (03) : 155 - 157
  • [9] RAMAN SPECTRA OF SULPHURIC, DEUTEROSULPHURIC, FLUOROSULPHURIC, CHLOROSULPHURIC, AND METHANESULPHONIC ACIDS AND THEIR ANIONS
    GILLESPIE, RJ
    ROBINSON, EA
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1962, 40 (04): : 644 - &
  • [10] Polyethersulfone sulfonated by chlorosulfonic acid and its membrane characteristics
    Guan, R
    Zou, H
    Lu, DP
    Gong, CL
    Liu, YF
    [J]. EUROPEAN POLYMER JOURNAL, 2005, 41 (07) : 1554 - 1560