A ring transformation of 6,7-dihydro-4H-pyrido[1,2-a]pyrimidin-4-ones

István Hermecz, Ágnes Horváth

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Under the conditions of Vilsmeier-Haack formylation, nitrogen bridgehead ring systems containing a 6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one moiety (which can isomerize into a tautomeric 6,7-dihydro from under the reaction conditions) or a 6,7-dihydro-4H-pyrido[1,2-a]-pyrimidin-4-one moiety undergo a ring transformation to afford the same nitrogen bridgehead nitrogen ring systems containing an unsaturated 4H-pyrido[1,2-a]pyrimidin-4-one moiety. Some details of the ring transformation were investigated by using deuterated and optically active derivatives. In the first step, a 7- dimethylaminomethylene-6,7-dihydro-4H-pyrido[1,2-a]pyrimidin-4-one species is formed, which is involved in the ring transformation.

Original languageEnglish
Pages (from-to)10221-10230
Number of pages10
JournalTetrahedron
Volume55
Issue number33
DOIs
Publication statusPublished - Aug 13 1999

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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