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1,4‐Piperazinium Hydrogen Sulfate {[H‐pi]HSO 4 } a Novel Di‐Cationic Ionic Liquid: Synthesis, Characterization and Its Applications as a Catalyst in Various Organic Transformations
Author(s) -
Jashnani S.,
Seddighi M.,
Langarudi M. S. N.,
Shirini F.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802639
Subject(s) - ionic liquid , chemistry , catalysis , cyclohexene , malononitrile , cationic polymerization , proton nmr , sulfuric acid , carbon 13 nmr , inorganic chemistry , organic chemistry , nuclear chemistry
In this work, a new nitrogen and sulfur based di‐cationic ionic liquid (IL), named 1,4‐piperazinium hydrogen sulfate ([H‐pi]HSO 4 ), was simply synthesized from the reaction of piperazine with sulfuric acid, and then characterized with a variety of techniques, including Infrared (IR) and Nuclear Magnetic Resonance (NMR) spectroscopies, Thermo‐gravimetric analysis (TGA), Scanning Electron Microscope (SEM), and pH analysis. This new ionic liquid was employed as an efficient catalyst for the synthesis of 2,2′‐arylmethylene‐bis(3‐hydroxy‐5,5‐dimethyl‐2‐cyclohexene‐1‐one) and 1,8‐dioxooctahydroxanthene derivatives in C 2 H 5 OH:H 2 O media and under solvent‐free conditions, respectively. Also, this adequate catalyst was employed for the synthesis of imidazo[1,2‐ a ]pyrimidines and triazolo[4,3‐ a ]pyrimidines via three‐component reaction of aldehydes, malononitrile and 2‐aminobenzimidazole and/or 3‐amino[1,2,4]triazole. The new functionally‐structured products, synthesized through these methods, were characterized with IR, 1 H NMR, 13 C NMR and mass spectroscopy. Moreover, the procedures gave the products in good yields and short reaction times as well as reusability of the catalyst.