Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides
Identifieur interne : 000211 ( Istex/Corpus ); précédent : 000210; suivant : 000212Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides
Auteurs : Todd Macklin ; Jane Panteleev ; Victor SnieckusSource :
- Angewandte Chemie [ 0044-8249 ] ; 2008-02-28.
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Abstract
Der Kreis schließt sich: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (3 und 4) aus 2‐But‐2‐inoylaryl‐O‐carbamaten 1 gelang über die gemeinsame Zwischenstufe 2. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B2pin2 führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.
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DOI: 10.1002/ange.200704360
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ISTEX:612FB0CAF4D91A731D30BF545C32F978C3BF4B73Le document en format XML
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wicri:corpus="ISTEX">000211</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Carbamoyl Translocations by an Anionic <hi rend="italic">ortho</hi>‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides<ref type="note" target="#nss"></ref></title><author><name sortKey="Macklin, Todd" sort="Macklin, Todd" uniqKey="Macklin T" first="Todd" last="Macklin">Todd Macklin</name><affiliation><mods:affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</mods:affiliation></affiliation></author><author><name sortKey="Panteleev, Jane" sort="Panteleev, Jane" uniqKey="Panteleev J" first="Jane" last="Panteleev">Jane Panteleev</name><affiliation><mods:affiliation>Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada</mods:affiliation></affiliation></author><author><name sortKey="Snieckus, Victor" sort="Snieckus, Victor" uniqKey="Snieckus V" first="Victor" last="Snieckus">Victor Snieckus</name><affiliation><mods:affiliation>E-mail: snieckus@chem.queensu.ca</mods:affiliation></affiliation><affiliation><mods:affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: snieckus@chem.queensu.ca</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Angewandte Chemie</title><title level="j" type="alt">ANGEWANDTE CHEMIE</title><idno type="ISSN">0044-8249</idno><idno type="eISSN">1521-3757</idno><imprint><biblScope unit="vol">120</biblScope><biblScope unit="issue">11</biblScope><biblScope unit="page" from="2127">2127</biblScope><biblScope unit="page" to="2131">2131</biblScope><biblScope unit="page-count">5</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2008-02-28">2008-02-28</date></imprint><idno type="ISSN">0044-8249</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0044-8249</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Angewandte chemie</term><term>Aryl</term><term>Chem</term><term>Chromone</term><term>Chromone product</term><term>Chromones</term><term>Corresponding aryl conditions</term><term>Cumulenolate</term><term>Entry base</term><term>Equiv</term><term>Lett</term><term>Ltmp</term><term>Ltmp sbuli</term><term>Michael addition</term><term>Products chemistry</term><term>Recent studies</term><term>Sbuli</term><term>Sbuli equiv</term><term>Snieckus</term><term>Tetrahedron lett</term><term>Verlag gmbh</term><term>Weinheim</term><term>Weinheim angew</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Angewandte chemie</term><term>Aryl</term><term>Chem</term><term>Chromone</term><term>Chromone product</term><term>Chromones</term><term>Corresponding aryl conditions</term><term>Cumulenolate</term><term>Entry base</term><term>Equiv</term><term>Lett</term><term>Ltmp</term><term>Ltmp sbuli</term><term>Michael addition</term><term>Products chemistry</term><term>Recent studies</term><term>Sbuli</term><term>Sbuli equiv</term><term>Snieckus</term><term>Tetrahedron lett</term><term>Verlag gmbh</term><term>Weinheim</term><term>Weinheim angew</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract">Der Kreis schließt sich: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (3 und 4) aus 2‐But‐2‐inoylaryl‐O‐carbamaten 1 gelang über die gemeinsame Zwischenstufe 2. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B2pin2 führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.</div></front></TEI><istex><corpusName>wiley</corpusName><keywords><teeft><json:string>equiv</json:string><json:string>ltmp</json:string><json:string>chem</json:string><json:string>chromone</json:string><json:string>lett</json:string><json:string>snieckus</json:string><json:string>sbuli</json:string><json:string>cumulenolate</json:string><json:string>weinheim</json:string><json:string>chromones</json:string><json:string>tetrahedron lett</json:string><json:string>verlag gmbh</json:string><json:string>ltmp sbuli</json:string><json:string>aryl</json:string><json:string>michael addition</json:string><json:string>sbuli equiv</json:string><json:string>recent studies</json:string><json:string>weinheim angew</json:string><json:string>chromone product</json:string><json:string>products chemistry</json:string><json:string>corresponding aryl conditions</json:string><json:string>angewandte chemie</json:string><json:string>entry base</json:string></teeft></keywords><author><json:item><name>Todd K. Macklin</name><affiliations><json:string>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</json:string></affiliations></json:item><json:item><name>Jane Panteleev</name><affiliations><json:string>Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada</json:string></affiliations></json:item><json:item><name>Victor Snieckus Prof.</name><affiliations><json:string>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</json:string><json:string>E-mail: snieckus@chem.queensu.ca</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Anionen</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Heterocyclen</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Metallierungen</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Organolithiumreagentien</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Synthesemethoden</value></json:item></subject><articleId><json:string>ANGE200704360</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>shortCommunication</json:string></originalGenre><abstract>Der Kreis schließt sich: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (3 und 4) aus 2‐But‐2‐inoylaryl‐O‐carbamaten 1 gelang über die gemeinsame Zwischenstufe 2. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B2pin2 führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.</abstract><qualityIndicators><score>3.503</score><pdfVersion>1.3</pdfVersion><pdfPageSize>595 x 842 pts (A4)</pdfPageSize><refBibsNative>true</refBibsNative><abstractCharCount>370</abstractCharCount><pdfWordCount>2987</pdfWordCount><pdfCharCount>18600</pdfCharCount><pdfPageCount>5</pdfPageCount><abstractWordCount>43</abstractWordCount></qualityIndicators><title>Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides</title><genre><json:string>brief-communication</json:string></genre><host><title>Angewandte Chemie</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1521-3757</json:string></doi><issn><json:string>0044-8249</json:string></issn><eissn><json:string>1521-3757</json:string></eissn><publisherId><json:string>ANGE</json:string></publisherId><volume>120</volume><issue>11</issue><pages><first>2127</first><last>2131</last><total>5</total></pages><genre><json:string>journal</json:string></genre><subject><json:item><value>Zuschrift</value></json:item></subject></host><publicationDate>2008</publicationDate><copyrightDate>2008</copyrightDate><doi><json:string>10.1002/ange.200704360</json:string></doi><id>612FB0CAF4D91A731D30BF545C32F978C3BF4B73</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/612FB0CAF4D91A731D30BF545C32F978C3BF4B73/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/612FB0CAF4D91A731D30BF545C32F978C3BF4B73/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/612FB0CAF4D91A731D30BF545C32F978C3BF4B73/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Carbamoyl Translocations by an Anionic <hi rend="italic">ortho</hi>‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides<ref type="note" target="#nss"></ref></title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><availability><licence>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</licence></availability><date type="published" when="2008-02-28"></date></publicationStmt><notesStmt><note type="content-type" subtype="brief-communication" source="shortCommunication" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="brief-communication"><analytic><title level="a" type="main" xml:lang="en">Carbamoyl Translocations by an Anionic <hi rend="italic">ortho</hi>‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides<ref type="note" target="#nss"></ref></title><author xml:id="author-0000"><persName><forename type="first">Todd K.</forename><surname>Macklin</surname></persName><affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/<address><country key="CA"></country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Jane</forename><surname>Panteleev</surname></persName><affiliation>Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada<address><country key="CA"></country></address></affiliation></author><author xml:id="author-0002"><persName><forename type="first">Victor</forename><surname>Snieckus</surname><roleName type="degree">Prof.</roleName></persName><email>snieckus@chem.queensu.ca</email><affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/<address><country key="CA"></country></address></affiliation></author><idno type="istex">612FB0CAF4D91A731D30BF545C32F978C3BF4B73</idno><idno type="ark">ark:/67375/WNG-FMZGN8WH-W</idno><idno type="DOI">10.1002/ange.200704360</idno><idno type="unit">ANGE200704360</idno><idno type="toTypesetVersion">file:ANGE.ANGE200704360.pdf</idno></analytic><monogr><title level="j" type="main">Angewandte Chemie</title><title level="j" type="alt">ANGEWANDTE CHEMIE</title><idno type="pISSN">0044-8249</idno><idno type="eISSN">1521-3757</idno><idno type="book-DOI">10.1002/(ISSN)1521-3757</idno><idno type="book-part-DOI">10.1002/ange.v120:11</idno><idno type="product">ANGE</idno><imprint><biblScope unit="vol">120</biblScope><biblScope unit="issue">11</biblScope><biblScope unit="page" from="2127">2127</biblScope><biblScope unit="page" to="2131">2131</biblScope><biblScope unit="page-count">5</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2008-02-28"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><abstract xml:lang="de" style="graphical"><p><hi rend="bold">Der Kreis schließt sich</hi>: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (<hi rend="bold">3</hi> und <hi rend="bold">4</hi>) aus 2‐But‐2‐inoylaryl‐<hi rend="italic">O</hi>‐carbamaten <hi rend="bold">1</hi> gelang über die gemeinsame Zwischenstufe <hi rend="bold">2</hi>. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B<hi rend="subscript">2</hi>pin<hi rend="subscript">2</hi> führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.<figure type="box"><media mimeType="image" url="urn:x-wiley:00448249:media:ANGE200704360:content"></media><media mimeType="image/gif" url="" rendition="webLoRes"></media><media mimeType="image/gif" url="" rendition="webOriginal"></media><media mimeType="image/gif" url="" rendition="webHiRes"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">Anionen</term><term xml:id="kwd2">Heterocyclen</term><term xml:id="kwd3">Metallierungen</term><term xml:id="kwd4">Organolithiumreagentien</term><term xml:id="kwd5">Synthesemethoden</term></keywords><keywords rend="articleCategory"><term>Zuschrift</term></keywords><keywords rend="tocHeading1"><term>Zuschriften</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/612FB0CAF4D91A731D30BF545C32F978C3BF4B73/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1521-3757</doi><issn type="print">0044-8249</issn><issn type="electronic">1521-3757</issn><idGroup><id type="product" value="ANGE"></id></idGroup><titleGroup><title type="main" xml:lang="de" sort="ANGEWANDTE CHEMIE">Angewandte Chemie</title><title type="short">Angew. 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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2007-09-21"></event><event type="firstOnline" date="2008-02-11"></event><event type="publishedOnlineFinalForm" date="2008-02-22"></event><event type="publishedOnlineAcceptedOrEarlyUnpaginated" date="2008-02-11"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.4.7 mode:FullText source:FullText result:FullText" date="2011-02-24"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-03"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-14"></event></eventGroup><numberingGroup><numbering type="pageFirst">2127</numbering><numbering type="pageLast">2131</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ANGE.ANGE200704360.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="40"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="54"></count></countGroup><titleGroup><title type="main" xml:lang="en">Carbamoyl Translocations by an Anionic <i>ortho</i>‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides<link href="#nss"></link></title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Todd K.</givenNames><familyName>Macklin</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#ab"><personName><givenNames>Jane</givenNames><familyName>Panteleev</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Victor</givenNames><familyName>Snieckus</familyName><degrees>Prof.</degrees></personName><contactDetails><email>snieckus@chem.queensu.ca</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="CA" type="organization"><unparsedAffiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 <url href="http://www.chem.queensu.ca/people/faculty/snieckus/">http://www.chem.queensu.ca/people/faculty/snieckus/</url></unparsedAffiliation></affiliation><affiliation xml:id="ab" countryCode="CA" type="organization"><unparsedAffiliation>Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Anionen</keyword><keyword xml:id="kwd2">Heterocyclen</keyword><keyword xml:id="kwd3">Metallierungen</keyword><keyword xml:id="kwd4">Organolithiumreagentien</keyword><keyword xml:id="kwd5">Synthesemethoden</keyword></keywordGroup><fundingInfo><fundingAgency>NSERC Canada</fundingAgency></fundingInfo><fundingInfo><fundingAgency>Merck Frosst Canada</fundingAgency></fundingInfo><fundingInfo><fundingAgency>NSERC</fundingAgency></fundingInfo><supportingInformation><p>Supporting information for this article is available on the WWW under <url href="http://www.wiley-vch.de/contents/jc_2001/2008/z704360_s.pdf">http://www.wiley‐vch.de/contents/jc_2001/2008/z704360_s.pdf</url> or from the author.</p></supportingInformation><abstractGroup><abstract type="graphical" xml:lang="de"><p><b>Der Kreis schließt sich</b>: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (<b>3</b> und <b>4</b>) aus 2‐But‐2‐inoylaryl‐<i>O</i>‐carbamaten <b>1</b> gelang über die gemeinsame Zwischenstufe <b>2</b>. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B<sub>2</sub>pin<sub>2</sub> führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:00448249:media:ANGE200704360:content"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/gif" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/gif" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta><noteGroup><note xml:id="nss"><p>We acknowledge with gratitude the NSERC Canada for support through the Discovery Grant program. We warmly thank Merck Frosst Canada for unrestricted grant support. J.P. would like to thank the NSERC for an Undergraduate Student Research Award (USRA).</p></note></noteGroup></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides</title></titleInfo><name type="personal"><namePart type="given">Todd K.</namePart><namePart type="family">Macklin</namePart><affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jane</namePart><namePart type="family">Panteleev</namePart><affiliation>Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Victor</namePart><namePart type="family">Snieckus</namePart><namePart type="termsOfAddress">Prof.</namePart><affiliation>E-mail: snieckus@chem.queensu.ca</affiliation><affiliation>Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada, Fax: (+1) 613‐533‐6089 http://www.chem.queensu.ca/people/faculty/snieckus/</affiliation><affiliation>E-mail: snieckus@chem.queensu.ca</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="shortCommunication" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-S9SX2MFS-0">brief-communication</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2008-02-28</dateIssued><dateCaptured encoding="w3cdtf">2007-09-21</dateCaptured><copyrightDate encoding="w3cdtf">2008</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">40</extent><extent unit="tables">1</extent><extent unit="references">54</extent></physicalDescription><abstract>Der Kreis schließt sich: Die regioselektive Synthese von Chromon‐3‐ und ‐8‐carboxamiden (3 und 4) aus 2‐But‐2‐inoylaryl‐O‐carbamaten 1 gelang über die gemeinsame Zwischenstufe 2. Wiederholte Metallierungen und eine iridiumkatalysierte Borylierung mit B2pin2 führten zu polysubstituierten Chromonen, die ein entscheidender Bestandteil vieler bioaktiver Verbindungen sind.</abstract><note type="content">*We acknowledge with gratitude the NSERC Canada for support through the Discovery Grant program. We warmly thank Merck Frosst Canada for unrestricted grant support. J.P. would like to thank the NSERC for an Undergraduate Student Research Award (USRA).</note><note type="funding">NSERC Canada</note><note type="funding">Merck Frosst Canada</note><note type="funding">NSERC</note><subject lang="en"><genre>keywords</genre><topic>Anionen</topic><topic>Heterocyclen</topic><topic>Metallierungen</topic><topic>Organolithiumreagentien</topic><topic>Synthesemethoden</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie</title></titleInfo><titleInfo type="abbreviated"><title>Angew. Chem.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> Supporting information for this article is available on the WWW under http://www.wiley‐vch.de/contents/jc_2001/2008/z704360_s.pdf or from the author.</note><subject><genre>article-category</genre><topic>Zuschrift</topic></subject><identifier type="ISSN">0044-8249</identifier><identifier type="eISSN">1521-3757</identifier><identifier type="DOI">10.1002/(ISSN)1521-3757</identifier><identifier type="PublisherID">ANGE</identifier><part><date>2008</date><detail type="volume"><caption>vol.</caption><number>120</number></detail><detail type="issue"><caption>no.</caption><number>11</number></detail><extent unit="pages"><start>2127</start><end>2131</end><total>5</total></extent></part></relatedItem><identifier type="istex">612FB0CAF4D91A731D30BF545C32F978C3BF4B73</identifier><identifier type="ark">ark:/67375/WNG-FMZGN8WH-W</identifier><identifier type="DOI">10.1002/ange.200704360</identifier><identifier type="ArticleID">ANGE200704360</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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