Abstract
Abstract A highly efficient multi-component one-pot synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives has been developed through the reaction of easily available aromatic aldehydes, benzoyl cyanide and either 2-aminoimidazole-4,5-dicarbonitrile or 3-amino-1,2,4-triazole in pyridine under controlled microwave heating. The process is environmentally friendly, is operationally simple, with short reaction time and with high yields.
Highlights
Nitrogen containing heterocycles widely occur in synthetic drugs and natural products
A highly efficient multi-component one-pot synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives has been developed through the reaction of available aromatic aldehydes, benzoyl cyanide and either 2-aminoimidazole-4,5-dicarbonitrile or 3-amino-1,2,4-triazole in pyridine under controlled microwave heating
In conjunction to our interest in performing green, general and efficient synthesis of biologically relevant heterocycles utilizing controlled microwave heating [20,21,22,23,24], we have developed convenient multi-component reaction for the synthesis of imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives
Summary
Nitrogen containing heterocycles widely occur in synthetic drugs and natural products. 1H-imidazo[1,2-a]imidazoles as [5 + 5] bicyclic guanidines exhibit a wide range of applications in fields related to pharmaceuticals and material science. Imidazo[1,2-a]imidazoles serve as lymphocyte function-associated nitrogen (LFA-1) inhibitors [4, 5], inhibiting [3H] diazepam binding [6]. Chiral imidazo[1,2-a] imidazoles act as a asymmetric catalyst in enantio-selective synthesis of α-amino nitriles and α-amino acids in Strecker reaction [8, 9]. Very limited reported strategies for the synthesis of imidazo[1,2-a]imidazoles are known. It mainly involves the construction of a α-bicyclic scaffold
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