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Synthesis 1987; 1987(3): 301-304
DOI: 10.1055/s-1987-27927
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Pyridinethiones XIV.1 Reactions of 2- and 4-Alkylthiopyridines; Synthesis of 1,6- and 2,7-Naphthyridines via 2-Methylene-1,2-dihydro- and 4-Methylene-1,4-dihydropyridines

Fahmy Mekhail Asaad* , Jan Becher, Jørgen Møller, Karikath Sukumar Varma
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publikationsdatum:
12. September 2002 (online)

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2,4-Bismethylthiopyridinium iodides prepared from 2(1 H)-pyridinethiones react regioselectively with active methylene compounds, preferentially at the 4-position, yielding 4-alkylidene-1,4-dihydropyridines. The corresponding 4-benzylthio-2-methylthiopyridinium iodide gave a mixture of 2-alkylidene-1,2-dihydro- and 4-alkylidene-1,4-dihydropyridines. By treatment with phosphoric acid, the resulting new 3-acetyl-2-alkyliden-1,2-dihydro- and 4-alkylidene-1,4-dihydropyridines yielded 1,6- and 2,7-naphthyridines, respectively.