ChemInform Abstract: Synthesis of 2-Functionalized N,N′-Dialkylimidazolium Salts from Glyoxal and Alkylamines.
Abstract
The diazadienes (I) which are easily prepared from aqueous glyoxal and the corresponding primary alkylamines (as described in the literature) react with dry hydrogen Chloride in non-aqueous solvents to form the azomethine derivatives (II) of the corresponding 2-formylimidazolium chlorides.
ChemInform Abstract
The diazadienes (I) which are easily prepared from aqueous glyoxal and the corresponding primary alkylamines (as described in the literature) react with dry hydrogen Chloride in non-aqueous solvents to form the azomethine derivatives (II) of the corresponding 2-formylimidazolium chlorides. (IIa), the structure ′of which was established by single-crystal X-ray diffraction, is hydrolyzed to give the aldehyde (III). (IIb) is converted directly under transamination to the corresponding 2-aminomethylimidazolium salt which is isolated as the hydrochloride (IV) (the mechanism of the formation of the imidazolium system is discussed). Using (IV) as an example, an improved routine APT method in 13C NMR spectroscopy is presented. It makes assignments more reliable in cases where unusual ′JCH couplings might occur.
