B. Trofimov, A. Mal’kina, O. Shemyakina
Sep 1, 2008
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Journal
Mendeleev Communications
Abstract
Isonicotinic acid is readily added to α,β-acetylenic γ-hydroxy nitriles through its nitrogen atom under mild non-catalytic conditions in water (50–55 °C, 45–50 h) to afford chemo-, regio- and stereospecifically 1-[(Z)-2-cyano-1-(1-hydroxy-1-alkylethyl)ethenyl]-pyridinium-4-carboxylates, densely functionalized derivatives of isonicotinic acid (45–90% yields). The structure and zwitterionic character of the adducts are proved by X-ray analysis.