Abstract
An easy synthesis of 1-aryl-1H -4,5-dihydroimidazoles 1 by cyclocondensation of N -aryl-N′ -formylethylenediamines 2 is described. Such precursors were synthesized by selective formylation of N -arylethylenediamines 3 with p -nitrophenyl formate. Cyclizations were performed using trimethylsilyl polyphosphate. Chemical properties of compounds 1 , typical of amidine system, were studied. Reaction of 1 with methyl iodide leads to the corresponding 1-aryl-3-methyl-1H -4,5-dihydroimidazolium salts 5 . Reduction of dihydroimidazoles 1 with sodium cyanoborohydride provides a convenient access to N- aryl-N′ -methylethylenediamines 4 .
Key words
heterocycles - nitrogen - cyclization - reductions - alkylations
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