SYNTHESIS AND PHOTOLYSIS OF N-PHTHALIMIDOAZIRIDINES WITH ELECTRON-WITHDRAWING SUBSTITUENTS

Abstract

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 endo-tricyclo[6.2.1.02,7]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.

How to Cite
Kuznetsov, M. A.; Ushkov, A. V.; Selivanov, S. I.; Kuznetsova, L. M.  Chem. Heterocycl. Compd. 2006, 42, 1143. [Khim. Geterotsikl. Soedin. 2006, 1320.]

For this article in the English edition see DOI 10.1007/s10593-006-0218-8