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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<profileDesc><abstract xml:lang="de" style="graphical"><p><hi rend="bold">Der Kreis schließt sich</hi>
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<keyword xml:id="kwd3">Metallierungen</keyword>
<keyword xml:id="kwd4">Organolithiumreagentien</keyword>
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<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>
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<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>
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<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>
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<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>
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<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>
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<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>
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<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>
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<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>
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<dateIssued encoding="w3cdtf">2008-02-28</dateIssued>
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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.</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>
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<identifier type="ISSN">0044-8249</identifier>
<identifier type="eISSN">1521-3757</identifier>
<identifier type="DOI">10.1002/(ISSN)1521-3757</identifier>
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<part><date>2008</date>
<detail type="volume"><caption>vol.</caption>
<number>120</number>
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<detail type="issue"><caption>no.</caption>
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