One-pot synthesis of 2-C-glycosylated benzimidazoles from the corresponding methanal dimethyl acetals.
A series of 2-glycosyl-benzimidazoles with alpha-d-arabinopyranosyl, beta-d-galactopyranosyl, beta-d-glucopyranosyl, beta-d-mannopyranosyl, and beta-l-rhamnopyranosyl configurations were obtained in 52-73% yields from the corresponding C-glycosylmethanal dimethyl acetals and o-phenylenediamine under catalysis with hydrogen chloride or a strongly acidic cation-exchange resin. Intermediate benzimidazolines were spontaneously oxidized by air to produce the final products in the one-pot procedure. The prepared compounds did not show any inhibitory effect on the growth of 12 strains of five different species of pathogenic yeasts.
Vojtech
Michal
M
Institute of Chemistry, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia.
Petrusová
Mária
M
Sláviková
Elena
E
Bekesová
Slávka
S
Petrus
Ladislav
L
D000080:Acetals / Q000737:chemistry*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure
D000080:Acetals; D001562:Benzimidazoles