Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to N-(3,5-dichlorophenyl)itaconimide

1,3-Dipolar Cycloaddition of Arylnitrile Oxides to Some Exocyclic Alkenes and Regioselective Synthesis of Spiro Isoxazolines

“…The most developed synthesis of these compounds depends mainly on cycloaddition reactions to exocyclic double bonds. [1][2][3][4][5][6] In the present work, we investigated the dipolar cycloaddition reactions of arylnitrile N-oxides to a number of arylmethylidenes derived from cycloalkanones, and attempted not only to study the regioselectivity of the reactions but also to isolate the biologically active spiroisoxazoline derivatives.…”

Reduction of 7-aryl-6,8-dioxo-2-oxa-3,7-diazabicyclo[3.3.0]oct-3-ene-4-carboxylic and 7-aryl-6,8-dioxo-1-oxa-2,7-diazaspiro[4.4]non-2-ene-3-carboxylic acid esters

“…It is known that the reduction of unsymmetrical bicyclic and spirocyclic imides (obtained by reaction of substituted benzonitrile oxides with N-arylmaleimides [3] and N- (3,5-dichlorophenyl)itaconimide [4]) at low temperature in the presence of Mg(ClO 4 ) 2 involves mainly the carbonyl group in the β-position with respect to the oxygen atom in the isoxazole ring.…”