Nucleophilic substitution reaction for arylglyoxal hydrates (AGs-hydrate) was studied via their reaction with some mono- and multi-nucleophilic reagents in the presence of sodium ethoxide as basic catalyst. Thus, reaction of phenylglyoxal hydrate (1a) with hydrogen sulfide and/or ammonium acetate afforded the corresponding 2-hydroxy-2-mercapto-1-phenylethanone (2) and 2-oxo-2-phenylethanimidamide (3), respectively. Heterocyclization reaction of AGs-hydrate 1a-f with 1-(1H-benzimidazol-2-yl)guanidine (4) gave 4-aroyl-[1,3,5]triazino[1,2-a]benzimidazol-2(1H)-imines 5a-f. Also, a series of 5-aryl-2-phenyl-4H-imidazol-4-imines 7a-d was synthesized via one-pot multicomponent reaction of AGs-hydrate 1a-d, benzonitrile (6) and ammonium acetate. Imidazole-4-imines 7a-d can be also prepared using other route via multicomponent reaction of AGs-hydrate 1a-d, benzenecarboximidamide acetate (8) and ammonium acetate.
Keywords: 4H-imidazol-4-imine; Arylglyoxal; Carboximidamide; Heterocyclization; Nucleophilic substitution; [1,3,5]triazino[1,2-a]benzimidazole.
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