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Utility of arylglyoxal hydrates in synthesis of 4-aroyl-[1,3,5]triazino[1,2-a]benzimidazol-2(1H)-imines and 5-aryl-2-phenyl-4H-imidazol-4-imines

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Abstract

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.

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  1. Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt

    Bahgat R. M. Hussein & Amr H. Moustafa

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Correspondence to Amr H. Moustafa.

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Hussein, B.R.M., Moustafa, A.H. Utility of arylglyoxal hydrates in synthesis of 4-aroyl-[1,3,5]triazino[1,2-a]benzimidazol-2(1H)-imines and 5-aryl-2-phenyl-4H-imidazol-4-imines. Mol Divers 26, 3185–3191 (2022). https://doi.org/10.1007/s11030-022-10379-8

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