Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA
作者： Leonardo Di Nunno , Paola Vitale , Antonio Scilimati
DOI: 10.1016/J.TET.2008.09.063
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摘要: Abstract 3-Arylisoxazoles react with LDA in THF at 0 °C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction arylnitriles may compete electronic and steric effects the substituent present aryl group being pivotal determining outcome this reaction. An interesting behaviour arising from fragmentation some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were fact formed (plausibly a benzyne mechanism) 3-(4-chlorophenyl)isoxazole 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine isolated starting 3-(2-methylphenyl)isoxazole LDA.
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