1372812-32-2Relevant academic research and scientific papers
Synthesis and synthetic applications of 1-aryl-2-alkyl-4,5-dihydro-1 H-imidazoles
Reverdito, Ana M.,Perillo, Isabel A.,Salerno, Alejandra
, p. 2083 - 2097 (2012/06/01)
An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.
