Synthesis of 2,3,5,6-Tetrasubstituted Pyridines from Enamines Derived from N,N-Dimethylformamide Dimethyl Acetal - Concepedia

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Synthesis of 2,3,5,6-Tetrasubstituted Pyridines from Enamines Derived from N,N-Dimethylformamide Dimethyl Acetal

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1995

Year

Fathi A. Abu‐Shanab, Alan D. Redhouse, J. R. Thompson, B. J. Wakefield

Derivative (Chemistry)1,3-Dicarbonyl CompoundsHeterocyclicN-dimethylformamide Dimethyl AcetalMalono-nitrile DimerOrganic ChemistryStereoselective SynthesisChemistryPharmacologyChemical DerivativeEnantioselective Synthesis2,3,5,6-Tetrasubstituted Pyridines

Abstract

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.