Abstract1‐Substituted benzimidazoles are readily annelated regio‐ and stereoselectively with α,β‐acetylenic γ‐hydroxyacidnitriles under mild conditions (20–25 °C, no catalyst, no solvent) to form new polyfunctional condensed systems, 4‐cyanomethylene‐1,3‐oxazolobenzimidazoles (30–88 % yield). Unexpectedly, the latter, when chromatographed on neutral Al2O3 at room temperature, undergo a complex multi‐position hydrolytic rearrangement involving the cleavage of the imidazole ring to aminophenyl N‐substituted formamides with an aminodihydrofuran moiety in the aminophenylsubstituent, N‐(2‐{[5‐amino‐2,2‐dialkyl‐3(2H)‐furanylidene]amino}phenyl)‐N‐substituted formamides, a novel class of highly functionalized pharmacophoric compounds. The results contribute to the basic benzimidazole chemistry and provide for prospective families of drug candidates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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