Stable azomethine imines derived from pyrazolidin-3-one and their cycloaddition to N-arylmaleimides

Abstract

Reactions of (Z)-1-arylmethylidene-3-oxopyrazolidin-1-ium-2-ides (stable analogs of azomethine imines generated by thermal opening of the diaziridine fragment in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes) with N-arylmaleimides having no ortho substituents in the aryl group are stereoselective: the products are mixtures of the corresponding cis and trans adducts, the latter prevailing (∼1.4–2.6: 1). trans Adducts are formed as the only products in the reactions with di-ortho-substituted N-arylmaleimides. (Z)-1-[(2,6-Dichlorophenyl) methylidene]-3-oxopyrazolidin-1-ium-2-ide reacts with both para- and ortho-substituted N-arylmaleimides to give exclusively trans adducts. Labile azomethine imines generated by thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes are likely to have Z configuration as well.