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- W2076183798 abstract "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." @default.
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- W2076183798 date "1995-03-01" @default.
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- W2076183798 title "Synthesis of 1-(dimethylsulfamoyl)-2- and 5-imidazolecarboxaldehydes. Rearrangement of 1-(dimethylsulfamoyl)-5-imidazole-carboxaldehyde to the 4-carboxaldehyde" @default.
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- W2076183798 doi "https://doi.org/10.1002/jhet.5570320241" @default.
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