Journal
SYNTHESIS-STUTTGART
Volume -, Issue 6, Pages 851-856Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2004-816011
Keywords
heterocycles; nitrogen; cyclization; reductions; alkylations
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An easy synthesis of 1-aryl-1 H-4,5-dihydroimidazoles 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-aryi-N'-methylethylenediamines 4.
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Anonymous
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