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DOI: 10.1055/s-2004-816011
Synthesis and Study of 1-Aryl-1H-4,5-dihydroimidazoles
Publication History
Publication Date:
15 March 2004 (online)
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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