Novel crown ether functionalized imidazolium-based acidic ionic liquid catalyzed synthesis of pyrazole derivatives under solvent-free conditions was written by Patil, Dayanand;Chandam, Dattatraya;Mulik, Abhijeet;Jagdale, Suryabala;Patil, Prasad;Deshmukh, Madhukar. And the article was included in Research on Chemical Intermediates in 2015.Product Details of 73387-46-9 This article mentions the following:
An innovative designed novel crown ether functionalized imidazolium-based reusable acidic ionic liquid [crown ether MIm] [HSO4] has been efficiently implemented for the synthesis of pyrazole derivatives using various substituted enaminones, hydrazine hydrate and Ph hydrazine under solvent-free conditions. Structural novelty and task efficiency of the catalyst, high yields of desired products, greener approach attributing high atom economy (green chem. method) and solvent-free conditions render this protocol suitable to cope with the current demand in contemporary organic chem. The inventive idea of utilizing crown ether functionalized ionic liquid as a catalyst was for the first time demonstrated in this protocol. The synthesis of the target compounds was achieved using [6-[1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl]hexyl]imidazolium sulfate as a catalyst. Starting materials included hydrazine, phenylhydrazine and enaminone derivatives [(amino)alkenone derivatives] such as 3-(dimethylamino)-1-phenyl-2-propen-2-one, 3-(dimethylamino)-1-(2-furanyl)-2-propen -1-one, 2-[(dimethylamino)methylene]-1,3-cyclohexanedione. The title compounds thus formed included pyrazole derivatives and analogs, such as 3-phenyl-1H-pyrazole, 3-(2-furanyl)-1H-pyrazole, 1,5,6,7-tetrahydro-4H-indazol-4-one (indazole derivatives). In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Product Details of 73387-46-9).
3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Product Details of 73387-46-9
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics