In:
European Journal of Organic Chemistry, Wiley, Vol. 2007, No. 6 ( 2007-02), p. 1018-1025
Abstract:
1‐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 Al 2 O 3 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(2 H )‐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)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2007:6
DOI:
10.1002/ejoc.200600776
Language:
English
Publisher:
Wiley
Publication Date:
2007
detail.hit.zdb_id:
1475010-7
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