A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones

Ivan V. Kulakov, Anton L. Shatsauskas, Mariya V. Matsukevich, Irina V. Palamarchuk, Tulegen M. Seilkhanov, Yuriy V. Gatilov, Alexander S. Fisyuk

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12 Citations (Scopus)

Abstract

A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[ c ][1,7]naphthyridin-4(3 H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1 H)-ones and aromatic aldehydes in a strong acidic media (trifluoroacetic, phosphorous or polyphosphorous acids) under heating. The initial imine derivatives undergo Pictet-Spengler condensation to form intermediate 6-aryl-5,6-dihydrobenzo[ c ]-1,7-naphthyridin-4(3 H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1 H)-ones as the final products.

Original languageEnglish
Pages (from-to)3700-3709
Number of pages10
JournalSynthesis (Germany)
Volume49
Issue number16
DOIs
Publication statusPublished - 16 Aug 2017

Keywords

  • intramolecular cyclization
  • naphthyridines
  • Pictet-Spengler reaction
  • pyridines
  • X-ray structural analysis

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