Thermolysis of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes in the Presence of N-Arylmaleimides

Heating of 6-aryl-1,5-diazabicyclo3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo1,2-a]pyrrolo3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1,3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1,5-diazabicyclo3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.