1250258-07-1Relevant academic research and scientific papers
Stereospecific synthesis of (Z)-1,3-oxazolobenzimidazoles from imidazole- and benzene-ring-substituted benzimidazoles and α,β-acetylenic γ-hydroxynitriles
Andriyankova, Ludmila V.,Belyaeva, Kseniya V.,Nikitina, Lina P.,Malkina, Anastasiya G.,Afonin, Andrei V.,Trofimov, Boris A.
experimental part, p. 2828 - 2834 (2010/10/02)
A stereospecific, facile synthesis of (Z)-1,3-oxazolobenzimidazoles from imidazole- and benzene-ring-substituted benzimidazoles and α,β- acetylenic γ-hydroxynitriles has been elaborated. The reaction proceeds smoothly in acetonitrile without catalyst (room temperature, 3-5 days or 35-40°C, 20-72 h) to afford the target compounds in 33-90% yields. The annulation involves an intermediate vinyl carbanion with zwitterionic character, which, after transformation into an O-centered zwitterion, is further inserted into the aromatic system of the imidazole ring. The synthesis contributes to the basic benzimidazole and acetylene chemistry and drug design. Georg Thieme Verlag Stuttgart.
