Synthesis and photolysis of N-phthalimidoaziridines with electron-withdrawing substituents

Mono-, bi-, tetra-, and pentacyclic N-phthalimidoaziridines with electron-withdrawing substituents in the three-membered ring have been obtained by the oxidative addition of N-aminophthalimide to dimethyl fumarate, ethyl cinnamate, N-phenyl-and N-benzylmaleimide, and endotricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-dione. Photolysis of 3-benzyl-6-phthalimido-3,6-diazabicyclo-[3.1.0]hexane-2,4-dione obtained in this way in the presence of dimethyl acetylenedicarboxylic acid (DMAD) gives in low yield the dimethyl ester of 3-benzyl-2,4-dioxo-8-phthalimido-3,8-diazabicyclo[3.2.1]oct-6-ene-6,7-dicarboxylic acid, the product of 1,3-dipolar cycloaddition to the N-phthalimidoazomethinylide formed as intermediate. However photolysis of this phthalimidoaziridine in the presence of other 1,3-dipolarophiles, like photolysis in the presence of DMAD of the remaining phalimidoaziridines, does not lead to a 1,3-dipolar cycloaddition product. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1320–1328, September, 2006.