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Main Title: ,, ... 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
Translated Title: "... and honour their art!" – evaluation of historical and new routes to 1,5-dihydroxy-6-oxo-1,6-dihydropyridine-2-carboxylic acid and 1,3-dihydroxy-2-oxo-3-pyrroline-4-carboxylic acid.
Author(s): Wiedemann, Dennis
Grohmann, Andreas
Type: Article
Language Code: en
Abstract: 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)]
Issue Date: 2009
Date Available: 13-Sep-2016
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Subject(s): lanthanoid chelators
2,5-Dioxohexanedioic acid
Journal Title: Zeitschrift für Naturforschung : B, a journal of chemical sciences
Publisher: De Gruyter
Publisher Place: Berlin
Volume: 64
Issue: 11-12
Publisher DOI: 10.1515/znb-2009-11-1206
Page Start: 1276
Page End: 1288
EISSN: 1865-7117
ISSN: 0932-0776
Appears in Collections:FG Anorganische Chemie - Festkörper- und Materialchemie » Publications

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