Lithiation of 1‐(dimethylsulfamoyl)imidazole by n‐butyllithium, followed by substitution with dimethylformamide provided 1‐(dimethylsulfamoyl)‐2‐imidazolecarboxaldehyde in 19% yield. When 1‐(dimethylsulfamoyl)‐2‐(tert‐butyldimethylsilyl)imidazole was lithiated by sec‐butyllithium, followed by methyl formate, there was obtained 1‐(dimethylsulfamoyl)‐2‐(tert‐butyldimethylsilyl)‐5‐imidazolecarbox‐aldehyde (57%). Removal of the silyl group by acetic acid yielded 1‐(dimethylsulfamoyl)‐5‐imidazolecarbxaldehyde (11, 96%) as a gum. Isomerization of 11 took place slowly at room temperature (10 days), or faster in tetrahydrofuran solution containing triethylamine (2 hours) to form crystalline 1‐(dimethylsul‐famoyl)‐4‐imidazolecarboxaldehyde (12) in 68% yield. Proton and carbon‐13 nmr spectra were analyzed to determine the structure of the isomers. However, only X‐ray crystallography established the structure of 1‐(dimethylsulfamoyl)‐4‐imidazolecarboxaldehyde, unequivocally. A mechanism for the isomerization of 11 to 12 is proposed.

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The Claisen‐Schmidt condensation of 1‐(triphenylmethyl)‐2‐imidazolecarboxaldehyde with acetophenones yielded 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]propen‐1‐ones 7. Selective catalytic hydrogenation over platinum of 7 furnished 1‐aryl‐3‐(2‐imidazolyl)‐1‐propanones 8. An alternate synthesis of 8 started with sodium borohydride reduction of 7 to give allylic alcohols, 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]‐2‐propen‐1‐ols 10, which were rearranged by hot aqueous sodium to 8. Acid hydrolysis of 8 provided the title compounds and triphenylmethanol.