One-pot, three-component synthesis of five-membered cyclic nitrones by addition/cyclization/condensation domino reaction

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 was tested. (C) 2010 Elsevier Ltd. All rights reserved.