ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Photochemistry of heterocycles. 24. Synthesis and photochemistry of 3-(2-pyridyl, 3-pyridyl, and 4-pyridyl)-substituted fused isoxazolines

V. Oremus, Ľ. Fišera, and N. Prónayová

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, CS-812 37 Bratislava

Abstract: 1,3-Dipolar cycloaddition of 2-, 3-, or 4-pyridinecarbonitrile oxide with 2,5-dihydrofuran, 5,6-bis(methoxycarbonyl)-7-oxabicyclo[2,2,l]hept-2-ene, and 2H,4H,7H-l,3-dioxepin is described. UV light irradiation of the thus prepared condensed isoxazolines furnished unstable enamino aldehydes. Quantum yields of the photolysis of the condensed isoxazolines increase in the series 2-, 4-, 3-pyridyl-substituted derivatives. Chemical structures of the condensed isoxazolines were inferred from the ^l3C NMR spectral data and the DQ COSY experiment in ¹H NMR spectra.

Full paper in Portable Document Format: 443a347.pdf

Chemical Papers 44 (3) 347–354 (1990)