Publikation:

Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water

Lade...
Vorschaubild

Dateien

Amaya-Garcia_2-k5ybi5oomg9z8.pdf
Amaya-Garcia_2-k5ybi5oomg9z8.pdfGröße: 3.4 MBDownloads: 89

Datum

2022

Herausgeber:innen

Kontakt

ISSN der Zeitschrift

Electronic ISSN

ISBN

Bibliografische Daten

Verlag

Schriftenreihe

Auflagebezeichnung

ArXiv-ID

Internationale Patentnummer

Link zur Lizenz

Angaben zur Forschungsförderung

Projekt

Open Access-Veröffentlichung
Open Access Hybrid
Core Facility der Universität Konstanz

Gesperrt bis

Titel in einer weiteren Sprache

Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published

Erschienen in

Synthesis. Georg Thieme Verlag. 2022, 54, pp. A-P. ISSN 0039-7881. eISSN 1437-210X. Available under: doi: 10.1055/s-0040-1719922

Zusammenfassung

Aromatic carboxylic acids are prone to decarboxylate in high-temperature water (HTW). While the decarboxylation kinetics of several aromatic carboxylic acids have been explored, studies on their compatibility with organic syntheses in HTW are scarce. Herein, we report the hydrothermal synthesis (HTS) of 2,3-diarylquinoxaline carboxylic acids from 1,2-diarylketones and 3,4-diaminobenzoic acid. A detailed study of the reaction parameters was performed to identify reaction conditions towards minimal decarboxylation. Thirteen 2,3-diarylquinoxaline-6-carboxylic acids are obtained at temperatures between 150–230 °C within 5–30 minutes. The reported conditions feature comparable performance to those of classic syntheses, avoiding volatile organic solvents, strong acids and toxic catalysts. Decarboxylated quinoxalines arise as side products in variable amounts via direct decarboxylation of the 3,4-diaminobenzoic acid. To completely inhibit the decarboxylation, we show that suitable structural analogues of 3,4-diaminobenzoic acid can act as starting compounds. Thus, ester hydrolysis of methyl 3,4-diaminobenzoate and deprotection of di-Boc-protected 3,4-diminobenzoic can be coupled with the HTS of quinoxaline towards quinoxaline carboxylic acids, while fully avoiding decarboxylated side products.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

quinoxalines, high-temperature water, green chemistry, decarboxylation, hydrothermal synthesis

Konferenz

Rezension
undefined / . - undefined, undefined

Forschungsvorhaben

Organisationseinheiten

Zeitschriftenheft

Zugehörige Datensätze in KOPS

Zitieren

ISO 690AMAYA GARCÍA, Fabián A., Miriam M. UNTERLASS, 2022. Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water. In: Synthesis. Georg Thieme Verlag. 2022, 54, pp. A-P. ISSN 0039-7881. eISSN 1437-210X. Available under: doi: 10.1055/s-0040-1719922
BibTex
@article{AmayaGarcia2022-06-07Synth-58017,
  year={2022},
  doi={10.1055/s-0040-1719922},
  title={Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water},
  volume={54},
  issn={0039-7881},
  journal={Synthesis},
  pages={A--P},
  author={Amaya García, Fabián A. and Unterlass, Miriam M.}
}
RDF
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/58017">
    <dc:creator>Unterlass, Miriam M.</dc:creator>
    <dcterms:abstract xml:lang="eng">Aromatic carboxylic acids are prone to decarboxylate in high-temperature water (HTW). While the decarboxylation kinetics of several aromatic carboxylic acids have been explored, studies on their compatibility with organic syntheses in HTW are scarce. Herein, we report the hydrothermal synthesis (HTS) of 2,3-diarylquinoxaline carboxylic acids from 1,2-diarylketones and 3,4-diaminobenzoic acid. A detailed study of the reaction parameters was performed to identify reaction conditions towards minimal decarboxylation. Thirteen 2,3-diarylquinoxaline-6-carboxylic acids are obtained at temperatures between 150–230 °C within 5–30 minutes. The reported conditions feature comparable performance to those of classic syntheses, avoiding volatile organic solvents, strong acids and toxic catalysts. Decarboxylated quinoxalines arise as side products in variable amounts via direct decarboxylation of the 3,4-diaminobenzoic acid. To completely inhibit the decarboxylation, we show that suitable structural analogues of 3,4-diaminobenzoic acid can act as starting compounds. Thus, ester hydrolysis of methyl 3,4-diaminobenzoate and deprotection of di-Boc-protected 3,4-diminobenzoic can be coupled with the HTS of quinoxaline towards quinoxaline carboxylic acids, while fully avoiding decarboxylated side products.</dcterms:abstract>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Amaya García, Fabián A.</dc:creator>
    <dc:contributor>Unterlass, Miriam M.</dc:contributor>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/58017/1/Amaya-Garcia_2-k5ybi5oomg9z8.pdf"/>
    <dc:language>eng</dc:language>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-12T10:02:00Z</dcterms:available>
    <dcterms:title>Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water</dcterms:title>
    <dc:rights>Attribution 4.0 International</dc:rights>
    <dc:contributor>Amaya García, Fabián A.</dc:contributor>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/58017/1/Amaya-Garcia_2-k5ybi5oomg9z8.pdf"/>
    <dcterms:issued>2022-06-07</dcterms:issued>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-12T10:02:00Z</dc:date>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by/4.0/"/>
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/58017"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
  </rdf:Description>
</rdf:RDF>

Interner Vermerk

xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter

Kontakt
URL der Originalveröffentl.

Prüfdatum der URL

Prüfungsdatum der Dissertation

Finanzierungsart

Kommentar zur Publikation

Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Ja
Begutachtet
Ja
Diese Publikation teilen