Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides
Identifieur interne : 000325 ( Istex/Corpus ); précédent : 000324; suivant : 000326Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides
Auteurs : Lucjan Strekowski ; Steven Patterson ; Marek T. Cegla ; Roman L. Wydra ; Agnieszka Czarny ; Donald B. HardenSource :
- Tetrahedron Letters [ 0040-4039 ] ; 1989.
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Abstract
Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.
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DOI: 10.1016/S0040-4039(01)93740-2
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ISTEX:4C193FA28184ED9E605FCB0682E8CE4EE3FE13AELe document en format XML
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Cegla</name><affiliation><mods:affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</mods:affiliation></affiliation></author><author><name sortKey="Wydra, Roman L" sort="Wydra, Roman L" uniqKey="Wydra R" first="Roman L." last="Wydra">Roman L. Wydra</name><affiliation><mods:affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</mods:affiliation></affiliation></author><author><name sortKey="Czarny, Agnieszka" sort="Czarny, Agnieszka" uniqKey="Czarny A" first="Agnieszka" last="Czarny">Agnieszka Czarny</name><affiliation><mods:affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</mods:affiliation></affiliation></author><author><name sortKey="Harden, Donald B" sort="Harden, Donald B" uniqKey="Harden D" first="Donald B." last="Harden">Donald B. Harden</name><affiliation><mods:affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="ISSN">0040-4039</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1989">1989</date><biblScope unit="volume">30</biblScope><biblScope unit="issue">39</biblScope><biblScope unit="page" from="5197">5197</biblScope><biblScope unit="page" to="5200">5200</biblScope></imprint><idno type="ISSN">0040-4039</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4039</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anion</term><term>Enamine</term><term>Ether</term><term>Ethyl ether</term><term>Lithiation reaction</term><term>Lithium</term><term>Lithium dialkylamides</term><term>Lithium diisopropylamide</term><term>Ltmp</term><term>Mmol</term><term>More sterically</term><term>Phcn</term><term>Quin</term><term>Resultant anion</term><term>Schiffs</term><term>Secondary enamines</term><term>Similar treatment</term><term>Sterically</term><term>Tetrahedron</term><term>Tetrahedron lett</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Anion</term><term>Enamine</term><term>Ether</term><term>Ethyl ether</term><term>Lithiation reaction</term><term>Lithium</term><term>Lithium dialkylamides</term><term>Lithium diisopropylamide</term><term>Ltmp</term><term>Mmol</term><term>More sterically</term><term>Phcn</term><term>Quin</term><term>Resultant anion</term><term>Schiffs</term><term>Secondary enamines</term><term>Similar treatment</term><term>Sterically</term><term>Tetrahedron</term><term>Tetrahedron lett</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>phcn</json:string><json:string>enamine</json:string><json:string>schiffs</json:string><json:string>tetrahedron</json:string><json:string>lithium</json:string><json:string>mmol</json:string><json:string>sterically</json:string><json:string>quin</json:string><json:string>ltmp</json:string><json:string>secondary enamines</json:string><json:string>tetrahedron lett</json:string><json:string>similar treatment</json:string><json:string>more sterically</json:string><json:string>lithium dialkylamides</json:string><json:string>lithiation reaction</json:string><json:string>resultant anion</json:string><json:string>lithium diisopropylamide</json:string><json:string>ethyl ether</json:string><json:string>ether</json:string><json:string>anion</json:string></teeft></keywords><author><json:item><name>Lucjan Strekowski</name><affiliations><json:string>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</json:string></affiliations></json:item><json:item><name>Steven Patterson</name><affiliations><json:string>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</json:string></affiliations></json:item><json:item><name>Marek T. Cegla</name><affiliations><json:string>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</json:string></affiliations></json:item><json:item><name>Roman L. Wydra</name><affiliations><json:string>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</json:string></affiliations></json:item><json:item><name>Agnieszka Czarny</name><affiliations><json:string>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</json:string></affiliations></json:item><json:item><name>Donald B. 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Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</note><affiliation>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</affiliation><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation></author><author xml:id="author-0003"><persName><forename type="first">Roman L.</forename><surname>Wydra</surname></persName><note type="biography">On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</note><affiliation>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</affiliation><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation></author><author xml:id="author-0004"><persName><forename type="first">Agnieszka</forename><surname>Czarny</surname></persName><note type="biography">On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</note><affiliation>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</affiliation><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation></author><author xml:id="author-0005"><persName><forename type="first">Donald B.</forename><surname>Harden</surname></persName><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation></author><idno type="istex">4C193FA28184ED9E605FCB0682E8CE4EE3FE13AE</idno><idno type="DOI">10.1016/S0040-4039(01)93740-2</idno><idno type="PII">S0040-4039(01)93740-2</idno></analytic><monogr><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="pISSN">0040-4039</idno><idno type="PII">S0040-4039(00)X0753-8</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1989"></date><biblScope unit="volume">30</biblScope><biblScope unit="issue">39</biblScope><biblScope unit="page" from="5197">5197</biblScope><biblScope unit="page" to="5200">5200</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1989</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</p></abstract><abstract style="graphical"><p>Lithiation with to give secondary enamines after quenching with H2Ogr1</p></abstract></profileDesc><revisionDesc><change when="1989">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/4C193FA28184ED9E605FCB0682E8CE4EE3FE13AE/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="gr1" NDATA="IMAGE" name="gr1"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla"><item-info><jid>TETL</jid><aid>01937402</aid><ce:pii>S0040-4039(01)93740-2</ce:pii><ce:doi>10.1016/S0040-4039(01)93740-2</ce:doi><ce:copyright type="unknown" year="1989"></ce:copyright></item-info><head><ce:title>Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides</ce:title><ce:author-group><ce:author><ce:given-name>Lucjan</ce:given-name><ce:surname>Strekowski</ce:surname><ce:ranking><ce:sup>∗</ce:sup></ce:ranking></ce:author><ce:author><ce:given-name>Steven</ce:given-name><ce:surname>Patterson</ce:surname></ce:author><ce:author><ce:given-name>Marek T.</ce:given-name><ce:surname>Cegla</ce:surname><ce:cross-ref refid="FN1"><ce:sup>1</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Roman L.</ce:given-name><ce:surname>Wydra</ce:surname><ce:cross-ref refid="FN1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Agnieszka</ce:given-name><ce:surname>Czarny</ce:surname><ce:cross-ref refid="FN1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Donald B.</ce:given-name><ce:surname>Harden</ce:surname></ce:author><ce:affiliation><ce:textfn>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</ce:textfn></ce:affiliation><ce:footnote id="FN1"><ce:label>1</ce:label><ce:note-para>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</ce:note-para></ce:footnote></ce:author-group><ce:date-received day="2" month="6" year="1989"></ce:date-received><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the <ce:italic>ortho</ce:italic> or <ce:italic>para</ce:italic> position of the aniline, but mediates tautomerization of the unsubstituted and <ce:italic>meta</ce:italic>-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>Lithiation with to give secondary enamines after quenching with H<ce:inf>2</ce:inf>O</ce:simple-para></ce:abstract-sec><ce:figure><ce:link locator="gr1"></ce:link></ce:figure></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides</title></titleInfo><name type="personal"><namePart type="given">Lucjan</namePart><namePart type="family">Strekowski</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Steven</namePart><namePart type="family">Patterson</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marek T.</namePart><namePart type="family">Cegla</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><description>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Roman L.</namePart><namePart type="family">Wydra</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><description>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Agnieszka</namePart><namePart type="family">Czarny</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><description>On leave of absence from the Institute of Pharmacology, 31–343 Cracow, Poland (M.T.C.); Institute of Natural Fibers, 60–630 Poznan, Poland (R.L.W.); and Department of Chemistry, Jagiellonian University, 30–060 Cracow, Poland (A.C.).</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Donald B.</namePart><namePart type="family">Harden</namePart><affiliation>Department of Chemistry, Georgia State University, Atlanta, Georgia 30303, USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1989</dateIssued><copyrightDate encoding="w3cdtf">1989</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.</abstract><abstract type="graphical">Lithiation with to give secondary enamines after quenching with H2Ogr1 </abstract><relatedItem type="host"><titleInfo><title>Tetrahedron Letters</title></titleInfo><titleInfo type="abbreviated"><title>TETL</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><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1989</dateIssued></originInfo><identifier type="ISSN">0040-4039</identifier><identifier type="PII">S0040-4039(00)X0753-8</identifier><part><date>1989</date><detail type="volume"><number>30</number><caption>vol.</caption></detail><detail type="issue"><number>39</number><caption>no.</caption></detail><extent unit="issue-pages"><start>5177</start><end>5376</end></extent><extent unit="pages"><start>5197</start><end>5200</end></extent></part></relatedItem><identifier type="istex">4C193FA28184ED9E605FCB0682E8CE4EE3FE13AE</identifier><identifier type="ark">ark:/67375/6H6-JSF0BQQ1-Q</identifier><identifier type="DOI">10.1016/S0040-4039(01)93740-2</identifier><identifier type="PII">S0040-4039(01)93740-2</identifier><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-HKKZVM7B-M">elsevier</recordContentSource></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/4C193FA28184ED9E605FCB0682E8CE4EE3FE13AE/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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|clé= ISTEX:4C193FA28184ED9E605FCB0682E8CE4EE3FE13AE
|texte= Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides
}}
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