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

Research output: Contribution to journalArticle

26 Citations (Scopus)


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
Issue number6
Publication statusPublished - 1990


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this