Journal of the Chemical Society. Perkin transactions I p. 2499 - 2502 (1994)
Update date:2022-08-11
Topics:
Croce, Piero Dalla
Ferraccioli, Raffaella
Rosa, Concetta La
The reaction of 2,4-diphenyl-4,5-dihydro-1,3-oxazol-5-one 1 with 4-phenyl-N-tosyl-1-azabuta-1,3-diene 2 has been investigated using different experimental conditions.Whereas at room temperature the kinetically controlled Michael adduct 3 was isolated, at 110 deg C products 4, 5, 6 and 7 were obtained.Their formation is explained according to 1,3-dipolar cycloaddition and nucleophilic addition, both related to the dual nature of the azlactone 1.The reactivity of azlactone 1 towards imine 2, which is different from that observed with N-alkyl- and N-aryl-1-azabuta-1,3-dienes, is explained on the basis of the electronic effects exerted by the tosyl substituent.
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