Zeitschrift fur Naturforschung, B: Chemical Sciences p. 809 - 817 (2015)
Update date:2022-07-30
Topics: Introduction Title Abstract Synthesis Section Spectroscopic Analysis Section Structural Investigation Section
Mohamed, Shaaban K.
Simpson, Jim
Marzouk, Adel A.
Talybov, Avtandil H.
Abdelhamid, Antar A.
Abdullayev, Yusif A.
Abbasov, Vagif M.
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 solventfree conditions and a green synthetic protocol. The key advantages of this process are high yield, shorter reaction times and ease of work-up. Fürthermore, 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.
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