Sterochemical Studies 107 Saturated heterocycles 111. Preparation of uracils via cycloreversion of norbornenefused pyrimidinediones

Gábor Bernáth, Géza Stájer, Angela E. Szabó, Zsolt Szóke-Molnár, Pál Sohár, Gyula Argay, Alajos Kálmán

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Abstract

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 I,1'-carbonyl-diimidazole to tricyclic quinazoline-2,4-dione (8a-e ), which decompose when heated, splitting off cyclopentadiene to yield 3-substituted uracils (14).

Original languageEnglish
Pages (from-to)1921-1930
Number of pages10
JournalTetrahedron
Volume43
Issue number8
DOIs
Publication statusPublished - 1987

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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