IndiumV2, Main, Exploration, bibRecord, 002C31

Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.

Identifieur interne : 002C31 ( Main/Exploration ); précédent : 002C30; suivant : 002C32

Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.

Auteurs : RBID : pubmed:16211116

English descriptors

KwdEn :
- Acrylates (chemistry), Acrylates (radiation effects), Alkylation, Amides (chemistry), Amides (radiation effects), Computer Simulation, Imines (chemistry), Imines (radiation effects), Indium (chemistry), Microwaves, Molecular Structure, Quinolines (chemical synthesis), Quinolines (chemistry), Quinolines (radiation effects), Stereoisomerism.
MESH :
- chemical , chemical synthesis : Quinolines.
- chemical , chemistry : Acrylates, Amides, Imines, Indium, Quinolines.
- chemical , radiation effects : Acrylates, Amides, Imines, Quinolines.
- Alkylation, Computer Simulation, Microwaves, Molecular Structure, Stereoisomerism.

Abstract

Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies.

DOI: 10.1039/b509400c
PubMed: 16211116

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Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.</title>
<author><name sortKey="Duvelleroy, Dorothee" uniqKey="Duvelleroy D">Dorothée Duvelleroy</name>
<affiliation wicri:level="3"><nlm:affiliation>Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS-ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen Cedex, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS-ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen Cedex</wicri:regionArea>
<placeName><region type="region" nuts="2">Basse-Normandie</region>
<settlement type="city">Caen</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Perrio, Cecile" uniqKey="Perrio C">Cécile Perrio</name>
</author>
<author><name sortKey="Parisel, Olivier" uniqKey="Parisel O">Olivier Parisel</name>
</author>
<author><name sortKey="Lasne, Marie Claire" uniqKey="Lasne M">Marie-Claire Lasne</name>
</author>
</titleStmt>
<publicationStmt><date when="2005">2005</date>
<idno type="doi">10.1039/b509400c</idno>
<idno type="RBID">pubmed:16211116</idno>
<idno type="pmid">16211116</idno>
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<idno type="wicri:Area/Main/Exploration">002C31</idno>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acrylates (chemistry)</term>
<term>Acrylates (radiation effects)</term>
<term>Alkylation</term>
<term>Amides (chemistry)</term>
<term>Amides (radiation effects)</term>
<term>Computer Simulation</term>
<term>Imines (chemistry)</term>
<term>Imines (radiation effects)</term>
<term>Indium (chemistry)</term>
<term>Microwaves</term>
<term>Molecular Structure</term>
<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Quinolines (radiation effects)</term>
<term>Stereoisomerism</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Acrylates</term>
<term>Amides</term>
<term>Imines</term>
<term>Indium</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="radiation effects" xml:lang="en"><term>Acrylates</term>
<term>Amides</term>
<term>Imines</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Alkylation</term>
<term>Computer Simulation</term>
<term>Microwaves</term>
<term>Molecular Structure</term>
<term>Stereoisomerism</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies.</div>
</front>
</TEI>
<pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">16211116</PMID>
<DateCreated><Year>2005</Year>
<Month>10</Month>
<Day>07</Day>
</DateCreated>
<DateCompleted><Year>2007</Year>
<Month>09</Month>
<Day>21</Day>
</DateCompleted>
<DateRevised><Year>2013</Year>
<Month>11</Month>
<Day>21</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">1477-0520</ISSN>
<JournalIssue CitedMedium="Print"><Volume>3</Volume>
<Issue>20</Issue>
<PubDate><Year>2005</Year>
<Month>Oct</Month>
<Day>21</Day>
</PubDate>
</JournalIssue>
<Title>Organic & biomolecular chemistry</Title>
<ISOAbbreviation>Org. Biomol. Chem.</ISOAbbreviation>
</Journal>
<ArticleTitle>Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.</ArticleTitle>
<Pagination><MedlinePgn>3794-804</MedlinePgn>
</Pagination>
<Abstract><AbstractText>Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Duvelleroy</LastName>
<ForeName>Dorothée</ForeName>
<Initials>D</Initials>
<Affiliation>Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS-ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen Cedex, France.</Affiliation>
</Author>
<Author ValidYN="Y"><LastName>Perrio</LastName>
<ForeName>Cécile</ForeName>
<Initials>C</Initials>
</Author>
<Author ValidYN="Y"><LastName>Parisel</LastName>
<ForeName>Olivier</ForeName>
<Initials>O</Initials>
</Author>
<Author ValidYN="Y"><LastName>Lasne</LastName>
<ForeName>Marie-Claire</ForeName>
<Initials>MC</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType>Journal Article</PublicationType>
<PublicationType>Research Support, Non-U.S. Gov't</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2005</Year>
<Month>09</Month>
<Day>09</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Org Biomol Chem</MedlineTA>
<NlmUniqueID>101154995</NlmUniqueID>
<ISSNLinking>1477-0520</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Acrylates</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Amides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Imines</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Quinolines</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>045A6V3VFX</RegistryNumber>
<NameOfSubstance>Indium</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>31JB8MKF8Z</RegistryNumber>
<NameOfSubstance>indium trichloride</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>486-74-8</RegistryNumber>
<NameOfSubstance>quinoline-4-carboxylic acid</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="Y">Acrylates</DescriptorName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
<QualifierName MajorTopicYN="N">radiation effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Alkylation</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="Y">Amides</DescriptorName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
<QualifierName MajorTopicYN="N">radiation effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Computer Simulation</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="Y">Imines</DescriptorName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
<QualifierName MajorTopicYN="N">radiation effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName>
<QualifierName MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Microwaves</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Quinolines</DescriptorName>
<QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
<QualifierName MajorTopicYN="N">radiation effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Stereoisomerism</DescriptorName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2005</Year>
<Month>9</Month>
<Day>9</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="epublish"><Year>2005</Year>
<Month>10</Month>
<Day>6</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2005</Year>
<Month>10</Month>
<Day>8</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2007</Year>
<Month>9</Month>
<Day>22</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2005</Year>
<Month>10</Month>
<Day>8</Day>
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<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="doi">10.1039/b509400c</ArticleId>
<ArticleId IdType="pubmed">16211116</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
</record>

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Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.

Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

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Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki