Tetrahedron p. 1921 - 1930 (1987)
Update date:2022-08-04
Topics:
Bernath, Gabor
Stajer, Geza
Szabo, Angela E.
Szoeke-Molnar, Zsolt
Sohar, Pal
et al.
From diexo-norbornane- and norbornene-azetidinones 5 and 6 with aryl isocyanates, N-arylcarbamoyl-substituted β-lactams (9 and 10) were prepared.The structures of the compounds were elucidated by IR, NMR spectroscopy and X-ray analysis, in comparison with saturated methylene-bridged quinazoline-2,4-diones (7a-b) prepared from norbornane-diexo-β-amino acid (1) with isocyanates and PPA.When heated with PPA, compounds 9 can be isomerized to 7.For preparation of the unsaturated compounds 8, the amino acid 2 was converted into the acid amides (13) and cyclized with 1,1'-carbonyl-diimidazole to tricyclic quinazoline-2,4-dione (8a-e), which decompose when heated, splitting off cyclopentadiene to yield 3-substituted uracils (14).
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Doi:10.1021/jo00270a027
(1989)Doi:10.1246/cl.1987.1361
(1987)Doi:10.1016/j.tetasy.2008.12.007
(2008)Doi:10.1002/jms.1462
(2008)Doi:10.1016/j.tet.2008.12.072
(2009)Doi:10.1246/bcsj.60.1564
(1987)