Collect. Czech. Chem. Commun.
1987, 52, 1773-1779
https://doi.org/10.1135/cccc19871773
Preparation and photochemistry of 3-cyanosubstituted condensed isoxazolines containing an oxygen atom
Vladimír Oremus, Lubor Fišera and Ladislav Štibrányi
Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava
Abstract
The 1,3-dipolar cycloaddition of cyanonitrile oxide to 2,3- and 2,5-dihydrofurane, 7-oxabicyclo[2,2,1]-2-heptene and derivatives of 1,3-dioxep-5-ene is described. The condensed isoxazolines Ia, IIIa, Va, Vc, Vd thus prepared are rearranged on irradiation into cyanosubstituted heterocyclic enaminoaldehydes IIa, IVa, VIa, VIc. The quantum yields of the photorearrangement of cyanoderivatives are higher than those of the phenyl derivatives, being within the limits from 0·068 to 0·19. The reaction of II with hydrazine gives the derivative IX of oxazino[4,5-d]pyridazine.
