Stereochemical studies, 144. Saturated heterocycles, 151 Preparation of cis and trans-cycloalkane-condensed pyrimidinediones by azetidinone ring transformation

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Abstract

N-substituted derivatives (3 and 4) obtained from cyclopentane- and cyclohexane-azetidinones (1 and 2) were isomerized with polyphosphoric acid to give cyclopentane-cis- (6) and cyclohexane-trans-condensed (7) 2,4pyrimidinediones. The structures of the dihydrouracils prepared by the ring transformation were proved by 1H- and 13C-nmr spectroscopy and by comparison with the compounds synthesized from cis- and trans-2-amino-1 -cycloalkanecarboxamides (11-13) with 1,1'-carbonyldiimidazole.

Original languageEnglish
Pages (from-to)1943-1950
Number of pages8
JournalTetrahedron
Volume46
Issue number6
DOIs
Publication statusPublished - 1990

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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