Multicomponent green synthesis, spectroscopic and structural investigation of multi-substituted imidazoles. Part 1

作者：Mohamed Shaaban K^*; Simpson Jim; Marzouk Adel A; Talybov Avtandil H; Abdelhamid Antar A; Abdullayev Yusif A; Abbasov Vagif M

来源：Zeitschrift Fur Naturforschung Section B-a Journal of Chemical Sciences, 2015, 70(11): 809-817.

DOI：10.1515/znb-2015-0067

• Bronsted acids
• green chemistry
• imidazoles
• ionic liquid
• molecular structures
• multicomponent reactions

Ten 1,2,4,5-tetra-substituted imidazole derivatives have been synthesized with a 2-hydroxyethy substituent at the 1-nitrogen atom and potentially electron releasing hydroxy-, methoxy-, dimethylamino-or nitro substituents in various positions on the benzene ring located on the 2-carbon atom. The prototypical derivative with an unsubstituted phenyl ring at the 2-position is also reported. The compounds are obtained in excellent yields (average 86 %) via a four-component cyclocondensation reaction of benzil, ethanolamine, and the appropriate aromatic carbaldehyde together with ammonium acetate. The reaction uses a novel ionic liquid catalyst, DEAHS (diethyl ammonium hydrogen sulfate), under solvent-free conditions and a green synthetic protocol. The key advantages of this process are high yield, shorter reaction times and ease of work-up. Furthermore, the products can be purified by a non-chromatographic method and the catalyst is re-usable. All of these newly synthesized compounds have been characterized from spectral data; the X-ray structures of three representative molecules are also detailed.

• 出版日期2015-11