Synthesis of partially saturated dipyrido[l,2-a:4,3-d] pyrimidin-11-ones via catalytic hydrogen-transfer reaction

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Abstract

1,2,3,4-Tetrahydrodipyrido[1,2-a:4,3-d] pyrimidin-11-ones (2-azapyracridones), a novel type of heterocycles, were synthesized by cyclization of 2-amino-6-methylpyridine with 3-methoxycarbony1-4-piperidone or its N-benzyl derivative. In the presence of palladium-on-carbon under mild conditions, the 2-azapyracridones undergo intermolecular hydrogen-transfer reactions. The product distributions can be shifted by applying solvents of proton donor or proton acceptor character; in this way, three differently saturated members of this ring system were prepared.

Original languageEnglish
Pages (from-to)1157-1160
Number of pages4
JournalTetrahedron
Volume43
Issue number6
DOIs
Publication statusPublished - 1987

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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