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Synthesis 2000; 2000(8): 1121-1124
DOI: 10.1055/s-2000-6325
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Synthesis of Dibenzo[c,h][1,6]naphthyridine, [2]Benzopyrano[4,3-c]quinoline and Benzo[i]phenanthridine Analogues of the Quaternary Benzo[c]phenanthridines

Susan M. Hutton* , Simon Paul Mackay, Otto Meth-Cohn
  • *Institute of Pharmacy and Chemistry, University of Sunderland, Sunderland, SR1 3SD, UK
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Publication Date:
31 December 2000 (online)

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Three concise syntheses of the dibenzo[c,h][1,6]naphthyridines, [2]benzopyrano[4,3-c]quinolines and the benzo[i]phenanthridines are reported. All methods involve Vilsmeier chemistry, either to generate a 12-methyl-6-oxo-6H-[2]benzopyrano[4,3-c]quinolinium salt which after hydrolysis with either ammonia or methanol can ultimately be cyclised to the first two target compounds, whereas the latter can be prepared in one step from 2-(1-pyrrolidino)-3,4-dihydronaphthalene and N-methylformanilide in phosphorus oxychloride. These tetracyclic heteroaromatic ring systems are related to the benzo[c]phenanthridines, and form part of our investigations into determining the mechanism of action of this class of compounds as topoisomerase inhibitors.

Vilsmeier reaction - quinolines - heterocycles - cyclisations - benzophenanthridines