Study of the Mechanism of the Alkylation of 2-Methylimidazole with 1,1,3,3-Tetraiodopropane-2-one by MALDI Mass Spectrometry

The mechanism of the alkylation of 2-methylimidazole with 1,1,3,3-tetraiodopropan-2-one in the absence and presence of HI acceptor (CaCO3) by matrix-assisted laser desorption/ionization mass spectrometry was studied for the first time. The composition of the reaction mixtures and possible routes of the formation of functionalized 2-methylimidazole derivatives were determined. The N1 and N1,3-alkylation of 2-methylimidazole with reduced (1-iodopropan-2-one, 1,3-diiodopropan-2-one) or dehydroiodinated (2,3-diiodo-2-cycloprop-1-ene) gives rise to forms 1,1, 3,3-tetraiodopropan-2-one is a key step in the synthesis. The thermodynamic and kinetic characteristics of the reduction and dehydroiodination of 1,1,3,3-tetraiodoacetone were evaluated by B3LYP/6-311+G(d,p)+dgdzvp) quantum-chemical calculations.