The reaction of nitrones with β-(2-aminophenyl) α,β-ynones in toluene at reflux temperature affords cis-fused isoxazolinoquinolines in moderate-to-high yields. This sequential process takes place throughregioselective 1,3-diploar cycloaddition of the nitrone to the triple bond followed by condensation between the amino and carbonyl groups.
Sequential 1,3-Dipolar Cycloaddition of Nitrones to β-(2-Aminophenyl) α,β-Ynones and Cyclocondensation : A New Entry to the Isoxazolino[4,5-c]quinoline Ring / G. Abbiati, A. Arcadi, F. Marinelli, E. Rossi, M. Verdecchia. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2009:7(2009 Jan), pp. 1027-1031. [10.1002/ejoc.200800994]
Sequential 1,3-Dipolar Cycloaddition of Nitrones to β-(2-Aminophenyl) α,β-Ynones and Cyclocondensation : A New Entry to the Isoxazolino[4,5-c]quinoline Ring
G. AbbiatiPrimo
;E. RossiPenultimo
;
2009
Abstract
The reaction of nitrones with β-(2-aminophenyl) α,β-ynones in toluene at reflux temperature affords cis-fused isoxazolinoquinolines in moderate-to-high yields. This sequential process takes place throughregioselective 1,3-diploar cycloaddition of the nitrone to the triple bond followed by condensation between the amino and carbonyl groups.
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