The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation
Identifieur interne : 000427 ( Istex/Corpus ); précédent : 000426; suivant : 000428The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation
Auteurs : Kristjan S. Gudmundsson ; John C. Drach ; Leroy B. TownsendSource :
- Tetrahedron Letters [ 0040-4039 ] ; 1996.
English descriptors
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Abstract
Abstract: A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (7) and the corresponding α-product (8). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.
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DOI: 10.1016/0040-4039(96)00292-4
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ISTEX:C2660CED4A6B6127116D97D435CAF24AD0E14514Le document en format XML
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Gudmundsson</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</mods:affiliation></affiliation></author><author><name sortKey="Drach, John C" sort="Drach, John C" uniqKey="Drach J" first="John C." last="Drach">John C. Drach</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</mods:affiliation></affiliation></author><author><name sortKey="Townsend, Leroy B" sort="Townsend, Leroy B" uniqKey="Townsend L" first="Leroy B." last="Townsend">Leroy B. Townsend</name><affiliation><mods:affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 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="1996">1996</date><biblScope unit="volume">37</biblScope><biblScope unit="issue">14</biblScope><biblScope unit="page" from="2365">2365</biblScope><biblScope unit="page" to="2368">2368</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>Ammonium chloride buffer</term><term>Anomeric</term><term>Chem</term><term>Elsevier science</term><term>Lewis acid</term><term>Lithiated</term><term>Reaction mixture</term><term>Reaction times</term><term>Ribosylation</term><term>Splitting pattern</term><term>Townsend</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Ammonium chloride buffer</term><term>Anomeric</term><term>Chem</term><term>Elsevier science</term><term>Lewis acid</term><term>Lithiated</term><term>Reaction mixture</term><term>Reaction times</term><term>Ribosylation</term><term>Splitting pattern</term><term>Townsend</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (7) and the corresponding α-product (8). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>chem</json:string><json:string>lithiated</json:string><json:string>ribosylation</json:string><json:string>anomeric</json:string><json:string>townsend</json:string><json:string>elsevier science</json:string><json:string>ammonium chloride buffer</json:string><json:string>lewis acid</json:string><json:string>reaction times</json:string><json:string>splitting pattern</json:string><json:string>reaction mixture</json:string></teeft></keywords><author><json:item><name>Kristjan S. Gudmundsson</name><affiliations><json:string>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</json:string></affiliations></json:item><json:item><name>John C. Drach</name><affiliations><json:string>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</json:string></affiliations></json:item><json:item><name>Leroy B. Townsend</name><affiliations><json:string>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</json:string></affiliations></json:item></author><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (7) and the corresponding α-product (8). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.</abstract><qualityIndicators><score>2.486</score><pdfVersion>1.2</pdfVersion><pdfPageSize>504 x 706 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>724</abstractCharCount><pdfWordCount>1442</pdfWordCount><pdfCharCount>9016</pdfCharCount><pdfPageCount>4</pdfPageCount><abstractWordCount>87</abstractWordCount></qualityIndicators><title>The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation</title><pii><json:string>0040-4039(96)00292-4</json:string></pii><genre><json:string>research-article</json:string></genre><host><title>Tetrahedron 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ribosylation</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>ELSEVIER</p></availability><date>1996</date></publicationStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a">The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation</title><author xml:id="author-0000"><persName><forename type="first">Kristjan S.</forename><surname>Gudmundsson</surname></persName><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</affiliation></author><author xml:id="author-0001"><persName><forename type="first">John C.</forename><surname>Drach</surname></persName><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</affiliation></author><author xml:id="author-0002"><persName><forename type="first">Leroy B.</forename><surname>Townsend</surname></persName><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</affiliation></author><idno type="istex">C2660CED4A6B6127116D97D435CAF24AD0E14514</idno><idno type="DOI">10.1016/0040-4039(96)00292-4</idno><idno type="PII">0040-4039(96)00292-4</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)X0019-6</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1996"></date><biblScope unit="volume">37</biblScope><biblScope unit="issue">14</biblScope><biblScope unit="page" from="2365">2365</biblScope><biblScope unit="page" to="2368">2368</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1996</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (7) and the corresponding α-product (8). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.</p></abstract><abstract style="graphical"><p>New C5 ribosylated imidazo[1,2-a]pyridine C-nucleoside 7 was synthesized from imidazo[1,2-a]pyridine (1) and ribonolactone (2).gr1</p></abstract></profileDesc><revisionDesc><change when="1996-01-31">Modified</change><change when="1996">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/C2660CED4A6B6127116D97D435CAF24AD0E14514/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>96002924</aid><ce:pii>0040-4039(96)00292-4</ce:pii><ce:doi>10.1016/0040-4039(96)00292-4</ce:doi><ce:copyright type="unknown" year="1996"></ce:copyright></item-info><head><ce:title>The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation</ce:title><ce:author-group><ce:author><ce:given-name>Kristjan S.</ce:given-name><ce:surname>Gudmundsson</ce:surname></ce:author><ce:author><ce:given-name>John C.</ce:given-name><ce:surname>Drach</ce:surname></ce:author><ce:author><ce:given-name>Leroy B.</ce:given-name><ce:surname>Townsend</ce:surname><ce:ranking><ce:sup>∗</ce:sup></ce:ranking></ce:author><ce:affiliation><ce:textfn>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</ce:textfn></ce:affiliation></ce:author-group><ce:date-received day="19" month="12" year="1995"></ce:date-received><ce:date-revised day="31" month="1" year="1996"></ce:date-revised><ce:date-accepted day="1" month="2" year="1996"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (<ce:bold>1</ce:bold>) with a protected ribonolactone (<ce:bold>2</ce:bold>), followed by acetylation to give the intermediate nucleoside <ce:bold>4</ce:bold>. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (<ce:bold>7</ce:bold>) and the corresponding α-product (<ce:bold>8</ce:bold>). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>New C5 ribosylated imidazo[1,2-a]pyridine C-nucleoside 7 was synthesized from imidazo[1,2-a]pyridine (<ce:bold>1</ce:bold>) and ribonolactone (<ce:bold>2</ce:bold>).</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>The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation</title></titleInfo><name type="personal"><namePart type="given">Kristjan S.</namePart><namePart type="family">Gudmundsson</namePart><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">John C.</namePart><namePart type="family">Drach</namePart><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 USA</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Leroy B.</namePart><namePart type="family">Townsend</namePart><affiliation>Department of Medicinal Chemistry, College of Pharmacy and Department of Chemistry, College of Literature, Science and the Arts, The University of Michigan, Ann Arbor, MI 48109-1065 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">1996</dateIssued><dateModified encoding="w3cdtf">1996-01-31</dateModified><copyrightDate encoding="w3cdtf">1996</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1,2-a]pyridine (7) and the corresponding α-product (8). The site of ribosylation was established with long range proton-carbon decoupling experiments. This ribosylation at C5 was entirely unexpected in view of previously reported condensations with lithiated imidazo[1,2-a]pyridines which occurred only at the C3 position.</abstract><abstract type="graphical">New C5 ribosylated imidazo[1,2-a]pyridine C-nucleoside 7 was synthesized from imidazo[1,2-a]pyridine (1) and ribonolactone (2).gr1 </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">19960401</dateIssued></originInfo><identifier type="ISSN">0040-4039</identifier><identifier type="PII">S0040-4039(00)X0019-6</identifier><part><date>19960401</date><detail type="volume"><number>37</number><caption>vol.</caption></detail><detail type="issue"><number>14</number><caption>no.</caption></detail><extent unit="issue-pages"><start>2315</start><end>2514</end></extent><extent unit="pages"><start>2365</start><end>2368</end></extent></part></relatedItem><identifier type="istex">C2660CED4A6B6127116D97D435CAF24AD0E14514</identifier><identifier type="ark">ark:/67375/6H6-KRFX9S6F-S</identifier><identifier type="DOI">10.1016/0040-4039(96)00292-4</identifier><identifier type="PII">0040-4039(96)00292-4</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/C2660CED4A6B6127116D97D435CAF24AD0E14514/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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