,, ... 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

dc.contributor.authorWiedemann, Dennis
dc.contributor.authorGrohmann, Andreas
dc.date.accessioned2016-09-13T12:02:45Z
dc.date.available2016-09-13T12:02:45Z
dc.date.issued2009
dc.description.abstractThe 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)]en
dc.identifier.eissn1865-7117
dc.identifier.issn0932-0776
dc.identifier.urihttp://depositonce.tu-berlin.de/handle/11303/5897
dc.identifier.urihttp://dx.doi.org/10.14279/depositonce-5490
dc.language.isoen
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/
dc.subject.ddc540 Chemie und zugeordnete Wissenschaftende
dc.subject.otherlanthanoid chelatorsen
dc.subject.other1,2-HOPOen
dc.subject.other2,5-Dioxohexanedioic aciden
dc.subject.other2,5-Dioxohexanedinitrileen
dc.subject.other5-Hydroxy-6-oxo-1,6-dihydropyridine-2-carboxamideen
dc.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-carbonsäurede
dc.title.translated"... 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.en
dc.typeArticleen
dc.type.versionpublishedVersionen
dcterms.bibliographicCitation.doi10.1515/znb-2009-11-1206
dcterms.bibliographicCitation.issue11-12
dcterms.bibliographicCitation.journaltitleZeitschrift für Naturforschung : B, a journal of chemical sciencesen
dcterms.bibliographicCitation.originalpublishernameDe Gruyteren
dcterms.bibliographicCitation.originalpublisherplaceBerlinen
dcterms.bibliographicCitation.pageend1288
dcterms.bibliographicCitation.pagestart1276
dcterms.bibliographicCitation.volume64
tub.accessrights.dnbfree
tub.affiliationFak. 2 Mathematik und Naturwissenschaften>Inst. Chemie>FG Anorganische Chemie - Festkörper- und Materialchemiede
tub.affiliation.facultyFak. 2 Mathematik und Naturwissenschaftende
tub.affiliation.groupFG Anorganische Chemie - Festkörper- und Materialchemiede
tub.affiliation.instituteInst. Chemiede
tub.publisher.universityorinstitutionTechnische Universität Berlin
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