Carbamoyl Translocations by an Anionic ortho‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides
Identifieur interne : 000203 ( Istex/Corpus ); précédent : 000202; suivant : 000204Carbamoyl 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 International Edition [ 1433-7851 ] ; 2008-02-28.
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Abstract
Completing the circle: A synthesis of chromone 3‐ and 8‐carboxamides (3 and 4) from 2‐but‐2‐ynoyl aryl O‐carbamates 1 has been achieved via common intermediate 2 in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B2pin2 borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.
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DOI: 10.1002/anie.200704360
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ISTEX:32A0F3C04FD8EA6C054F332BDB9B603D299BA395Le document en format XML
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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">32A0F3C04FD8EA6C054F332BDB9B603D299BA395</idno><idno type="ark">ark:/67375/WNG-5DNNBQ4Q-P</idno><idno type="DOI">10.1002/anie.200704360</idno><idno type="unit">ANIE200704360</idno><idno type="toTypesetVersion">file:ANIE.ANIE200704360.pdf</idno></analytic><monogr><title level="j" type="main">Angewandte Chemie International Edition</title><title level="j" type="alt">ANGEWANDTE CHEMIE INTERNATIONAL EDITION</title><idno type="pISSN">1433-7851</idno><idno type="eISSN">1521-3773</idno><idno type="book-DOI">10.1002/(ISSN)1521-3773</idno><idno type="book-part-DOI">10.1002/anie.v47:11</idno><idno type="product">ANIE</idno><imprint><biblScope unit="vol">47</biblScope><biblScope unit="issue">11</biblScope><biblScope unit="page" from="2097">2097</biblScope><biblScope unit="page" to="2101">2101</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="en" style="graphical"><p><hi rend="bold">Completing the circle</hi>: A synthesis of chromone 3‐ and 8‐carboxamides (<hi rend="bold">3</hi> and <hi rend="bold">4</hi>) from 2‐but‐2‐ynoyl aryl <hi rend="italic">O</hi>‐carbamates <hi rend="bold">1</hi> has been achieved via common intermediate <hi rend="bold">2</hi> in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B<hi rend="subscript">2</hi>pin<hi rend="subscript">2</hi> borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.<figure type="box"><media mimeType="image" url="urn:x-wiley:14337851:media:ANIE200704360: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">anionic reactions</term><term xml:id="kwd2">heterocycles</term><term xml:id="kwd3">metalation</term><term xml:id="kwd4">organolithium reagents</term><term xml:id="kwd5">synthetic methods</term></keywords><keywords rend="articleCategory"><term>Communication</term></keywords><keywords rend="tocHeading1"><term>Communications</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/32A0F3C04FD8EA6C054F332BDB9B603D299BA395/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)1521-3773</doi><issn type="print">1433-7851</issn><issn type="electronic">1521-3773</issn><idGroup><id type="product" value="ANIE"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="ANGEWANDTE CHEMIE INTERNATIONAL EDITION">Angewandte Chemie International Edition</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">2097</numbering><numbering type="pageLast">2101</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ANIE.ANIE200704360.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">anionic reactions</keyword><keyword xml:id="kwd2">heterocycles</keyword><keyword xml:id="kwd3">metalation</keyword><keyword xml:id="kwd4">organolithium reagents</keyword><keyword xml:id="kwd5">synthetic methods</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_2002/2008/z704360_s.pdf">http://www.wiley‐vch.de/contents/jc_2002/2008/z704360_s.pdf</url> or from the author.</p></supportingInformation><abstractGroup><abstract type="graphical" xml:lang="en"><p><b>Completing the circle</b>: A synthesis of chromone 3‐ and 8‐carboxamides (<b>3</b> and <b>4</b>) from 2‐but‐2‐ynoyl aryl <i>O</i>‐carbamates <b>1</b> has been achieved via common intermediate <b>2</b> in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B<sub>2</sub>pin<sub>2</sub> borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:14337851:media:ANIE200704360: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>Completing the circle: A synthesis of chromone 3‐ and 8‐carboxamides (3 and 4) from 2‐but‐2‐ynoyl aryl O‐carbamates 1 has been achieved via common intermediate 2 in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B2pin2 borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.</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>anionic reactions</topic><topic>heterocycles</topic><topic>metalation</topic><topic>organolithium reagents</topic><topic>synthetic methods</topic></subject><relatedItem type="host"><titleInfo><title>Angewandte Chemie International Edition</title></titleInfo><titleInfo type="abbreviated"><title>Angew. Chem. Int. Ed.</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_2002/2008/z704360_s.pdf or from the author.</note><subject><genre>article-category</genre><topic>Communication</topic></subject><identifier type="ISSN">1433-7851</identifier><identifier type="eISSN">1521-3773</identifier><identifier type="DOI">10.1002/(ISSN)1521-3773</identifier><identifier type="PublisherID">ANIE</identifier><part><date>2008</date><detail type="volume"><caption>vol.</caption><number>47</number></detail><detail type="issue"><caption>no.</caption><number>11</number></detail><extent unit="pages"><start>2097</start><end>2101</end><total>5</total></extent></part></relatedItem><identifier type="istex">32A0F3C04FD8EA6C054F332BDB9B603D299BA395</identifier><identifier type="ark">ark:/67375/WNG-5DNNBQ4Q-P</identifier><identifier type="DOI">10.1002/anie.200704360</identifier><identifier type="ArticleID">ANIE200704360</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. 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