A. V. Denisenko, A. V. Tverdokhlebov, A. Tolmachev
Mar 1, 2010
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5
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Synthesis
Abstract
5'-Substituted 2-(2-amino-3-furanyl)-1,3-dimethyl-1H-benzimidazolium bromides were obtained in excellent yields upon heating (1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-ylidene)acetonitrile with α-bromo ketones in refluxing N,N-dimethylformamide. Reduction of the prepared quaternary salts with sodium borohydride afforded 5-substituted 3-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)-2-furanamines. The latter were shown to be masked amino aldehydes. Thus, the corresponding 2-amino-3-furancarboxaldehyde phenylhydrazones and semicarbazones were obtained upon treatment with phenylhydrazine and semicarbazide, respectively, whereas condensation with malononitrile yielded 2-substituted 6-aminofuro[2,3-b]pyridine-5-carbonitriles.