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A new approach to five-membered cyclic nitrones connected with the incorporation of a planar aromatic ring system into the structure is described. This procedure is based on an allenyloxime one-pot domino transformation under simple base catalysis in alcoholic and aqueous solvents. The structure of obtained nitrones was studied by X-ray analysis and the reactivity of products in 1,3-dipolar cycloadditions...
A variety of conditions including reductive and/or basic reagents in aqueous or alcoholic solution was applied to 2,2-dimethylpenta-3,4-dienal oxime. Formation of various five-membered heterocycles with excellent chemical selectivity was observed. Most of the reactions yielded cyclic nitrones with stable dipolar structure and unique functionalities present. All products of cyclization were isolated...
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