R. Hernandez et al., NOVEL HETEROCYCLIC OUTER-RING DIENES - N-ALKYL-SUBSTITUTED 4,5-DIMETHYLENE-2-OXAZOLIDINONE AND N-ARYL-SUBSTITUTED 4,5-DIMETHYLENE-2-OXAZOLIDINONE, Heterocycles, 36(9), 1993, pp. 1951-1956
The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimeth
ylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocya
nate in the presence of triethylamine is described. Diene (4a) undergo
es Diels-Alder cycloaddition with N-phenylmaleimide (10), and, in the
absence of a dienophile, gives a mixture of dimers (12) and (13), and
the ring closure cyclobutene (14).