Steric control of reactivity: formation of oximes, benzodiazepinone n-oxides and isoxazoloquinolinones
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Heaney, Frances; Bourke, Sharon; Cunningham, Desmond; McArdle, Patrick (1998). Steric control of reactivity: formation of oximes, benzodiazepinone n-oxides and isoxazoloquinolinones. Journal of the Chemical Society, Perkin Transactions 2 (3), 547-559
Reaction of the alkenyl carbonyl compounds 1 with hydroxylamine can lead to the formation of the oximes 2, the benzodiazepinone N-oxides 3 or the isoxazoloquinolinones 5. The product(s) of reaction are shown to depend on the electronic nature of the terminal olefinic substituent R-3 and the space filling capacity of the substituents R-1, R-2 and R-4. When the olefinic centre is electron poor (R-3 = CO2Et) ketocarbonyls convert exclusively to bicyclic nitrones 3 whereas aldehydes are more sensitive to subtle changes in skeletal structure and give rise to oximes 2, tricycles 5 or mixtures of both, For aldehyde and ketone substrates when the olefinic centre carries an aryl substituent (R-3 = Ph) the primary product of reaction is the corresponding oxime which on thermal activation converts to the tricyclic isoxazoloquinolinones.