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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)

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