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Report | Regular issue | Vol 23, No. 5, 1985, pp.1155-1160
Published online, 1st January, 1970
DOI: 10.3987/R-1985-05-1155
■ Reaction of Azomethine N-Oxides. Part 4. A New Mode of Reaction of Azomethine N-Oxides with Dibenzoylacetylene

Ahmed Moukhtar Nour El-Din,* Aboul-Fetouh El-Said Mourad, and Ramadan Mekamer

*Chemistry Department, Faculty of Science, El-Minia University, El-Minia 61519, Egypt

Abstract

A new mode of 1,3-dipolar cycloaddition reaction with dibenzoylacetylene as dipolarophile was observed. The addition of this dipolarophile to different substituted open chain N-arylnitrones afforded 3-anilino-1,4-diphenylbutane-1,2,4-trione. Its formation by 1,3-dipolar cycloaddition reaction followed by interamolecular rearrangement and ylide decomposition is discussed. On the other hand, the conformationally rigid cyclic nitrones form either 4-oxazoline or enamine compounds.