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Synthesis 1995; 1995(5): 557-560
DOI: 10.1055/s-1995-3954
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Synthesis of 2,3,5,6-Tetrasubstituted Pyridines from Enamines Derived from N,N-Dimethylformamide Dimethyl Acetal

Fathi A. Abu-Shanab, Alan D. Redhouse, J. Robin Thompson, Basil J. Wakefield*
  • *Department of Chemistry and Applied Chemistry, Cockcroft Building, University of Salford, Salford M5 4WT, England, Fax +44(161)7455111; E-mail b.j.wakefield@chemistry.Salford.ac.uk
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Publikationsdatum:
31. Dezember 2000 (online)

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Reactions of 1,3-dicarbonyl compounds with N,N-dimethylformamide dimethyl acetal, followed by cyanothioacetamide or cyanoacetamide and sodium hydride, then acidification, give 5,6-disubstituted 3-cyanopyridine-2(1H)-thiones or 5,6-disubstituted 3-cyanopyridin-2(1H)-ones 4. Analogous reactions with the malono-nitrile dimer give 5,6-disubstituted 3-cyano-2-(dicyanomethylene)-1,2-dihydropyridines 9.

1,3-dicarbonyl - N,N-dimethylformamide dimethyl acetal - enamine - cyanoacetamide - cyanothioacetamide - cyanopyridinethione - cyanopyridinone - 2-(dicyanomethylene)pyridine

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