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Communication | Regular issue | Vol 36, No. 9, 1993, pp.1951-1956
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6407
Novel Heterocyclic Outer-Ring Dienes: N-Alkyl- and N-Aryl Substituted 4,5-Dimethylene-2-oxazolidinones

Raúl Hernández, José M. Sánchez, Adriana Gómez, Gonzalo Trujillo, Rossana Aboytes, Gerardo Zepeda, Roderick W. Bates, and Joaquín Tamariz*

*Departamento de Químíca Orgánica, Escuela Nacional de Ciencias Biológicas, I. P. N., Prol. Carpio y Plan de Ayala S/N,11340, Mexico, D.F.


The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimethylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocyanate in the presence of triethylamine is described. Diene (4a) undergoes 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).