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Facile synthesis of new imidazoles from direct reaction of 2,3‐diamino‐1,4‐naphthoquinone with aldehydes
Author(s) -
Aly Ashraf A.,
Hassan Alaa A.,
Brown Alan B.,
ElShaieb Kamal M.,
Bedair Tarek M. I.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.582
Subject(s) - chemistry , yield (engineering) , dimethyl sulfoxide , acetic acid , 1,4 naphthoquinone , stoichiometry , imidazole , solvent , naphthoquinone , organic chemistry , combinatorial chemistry , medicinal chemistry , metallurgy , materials science
New imidazoles were easily prepared from 2,3‐diamino‐1,4‐naphthoquinone and stoichiometric quantities of the appropriate aldehydes in dimethyl sulfoxide as a solvent. The reaction proceeded for few hours. The procedure can be generalized to different classes of aldehydes. 2‐Methyl‐1 H ‐naphtho[2,3‐ d ]imidazole‐4,9‐dione was also obtained in good yield during refluxing of 2,3‐diaminonaphthoquinone in acetic acid. The structure of the newly synthesized imidazoles was extensively investigated using NMR experiments. J. Heterocyclic Chem., (2011).