Reactions of electron-poor α-haloketones with (N-isocyanimino)

The 1:1 imine intermediate generated by the addition of benzyl amine to cyclobutanone is trapped by (N-isocyanimino)triphenylphosphorane in the presence of an aromatic carboxylic acid leads to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives, were produced in excellent yields.

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The 1 : 1 imine intermediate 7 generated by the addition of a primary amine 2 to chloroacetone (1) is trapped by (isocyanoimino)triphenylphosphorane (4) in the presence of an aromatic carboxylic acid 3 and leads to the formation of the corresponding iminophosphorane intermediate 9 (Scheme 2). The 1,3,4-oxadiazole derivatives 5 are then formed via an intramolecular aza-Wittig reaction of the iminophosphorane intermediate 9. The reactions were completed under neutral conditions at room temperature. The fully substituted 1,3,4-oxadiazole derivatives 5 were produced in high yields (Table).