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,, ... und ehrt mir ihre Kunst!“ – Evaluierung historischer und neuer Synthesewege zu 1,5-Dihydroxy-6-oxo-1,6-dihydropyridin-2-carbonsäure und 1,3-Dihydroxy-2-oxo-3-pyrrolin-4-carbonsäure

Wiedemann, Dennis; Grohmann, Andreas

The historical and recent literature describing synthetical pathways to the title compds. is comprehensively summarized and evaluated. Routes via 2,5-dioxoadipic acid or 2,5-dihydroxymuconic acid as intermediates could not be followed reproducibly. 3-Hydroxy-2-oxo-2H-pyran-6-carboxylic acid and Et 3-hydroxy-2-oxo-3-pyrroline-4-carboxylate (I) were fully characterized by spectroscopic methods and single-crystal x-ray diffraction. Both compds. have an enolic structure in soln. as well as in the solid state. A recently published ring-closing metathesis (RCM) protocol to a deriv. of the first title compd. was unproductive in the authors' hands. The authors present a new two-step synthesis of the similarly substituted 5-hydroxy-6-oxo-1,6-dihydropyridine-2-carboxamide (II) using succinyl cyanide. The product was identified and characterized by spectroscopic methods and x-ray crystallog. [on SciFinder(R)]
Published in: Zeitschrift für Naturforschung : B, a journal of chemical sciences, 10.1515/znb-2009-11-1206, De Gruyter