Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization
Identifieur interne : 000697 ( Istex/Corpus ); précédent : 000696; suivant : 000698Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization
Auteurs : Alain Fogain-Ninkam ; Adam Daïch ; Bernard Decroix ; Pierre NetchitaïloSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2003-11.
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Abstract
Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
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DOI: 10.1002/ejoc.200300072
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J. Org. Chem.</title><idno type="ISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><imprint><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2003-11">2003-11</date><biblScope unit="volume">2003</biblScope><biblScope unit="issue">21</biblScope><biblScope unit="page" from="4273">4273</biblScope><biblScope unit="page" to="4278">4278</biblScope></imprint><idno type="ISSN">1434-193X</idno></series><idno type="istex">6A018384956A55AEAE822799E4A059255DEFAED3</idno><idno type="DOI">10.1002/ejoc.200300072</idno><idno type="ArticleID">EJOC200300072</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1434-193X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkaloids</term><term>Cyclization</term><term>Nitrogen heterocycles</term><term>Reduction</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Alain Fogain‐Ninkam</name><affiliations><json:string>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</json:string></affiliations></json:item><json:item><name>Adam Daïch</name><affiliations><json:string>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</json:string></affiliations></json:item><json:item><name>Bernard Decroix</name><affiliations><json:string>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</json:string></affiliations></json:item><json:item><name>Pierre Netchitaïlo</name><affiliations><json:string>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</json:string><json:string>E-mail: pierre.netchitailo@univ‐lehavre.fr</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Alkaloids</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Cyclization</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Nitrogen heterocycles</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Reduction</value></json:item></subject><articleId><json:string>EJOC200300072</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><abstract>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. 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J. Org. Chem.</title><idno type="pISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><idno type="DOI">10.1002/(ISSN)1099-0690</idno><imprint><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2003-11"></date><biblScope unit="volume">2003</biblScope><biblScope unit="issue">21</biblScope><biblScope unit="page" from="4273">4273</biblScope><biblScope unit="page" to="4278">4278</biblScope></imprint></monogr><idno type="istex">6A018384956A55AEAE822799E4A059255DEFAED3</idno><idno type="DOI">10.1002/ejoc.200300072</idno><idno type="ArticleID">EJOC200300072</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2003</date></creation><langUsage><language ident="en">en</language></langUsage><abstract><p>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>keywords</head><item><term>Alkaloids</term></item><item><term>Cyclization</term></item><item><term>Nitrogen heterocycles</term></item><item><term>Reduction</term></item></list></keywords></textClass><textClass><keywords scheme="Journal Subject"><list><head>article-category</head><item><term>Full Paper</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2003-02-06">Received</change><change when="2003-11">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><original>false</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/6A018384956A55AEAE822799E4A059255DEFAED3/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)1099-0690</doi><issn type="print">1434-193X</issn><issn type="electronic">1099-0690</issn><idGroup><id type="product" value="EJOC"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="EUROPEAN JOURNAL OF ORGANIC CHEMISTRY">European Journal of Organic Chemistry</title><title type="short">Eur. 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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2003-02-06"></event><event type="firstOnline" date="2003-10-22"></event><event type="publishedOnlineFinalForm" date="2003-10-22"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.6 mode:FullText source:FullText result:FullText mathml2tex" date="2010-04-20"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-24"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-16"></event></eventGroup><numberingGroup><numbering type="pageFirst">4273</numbering><numbering type="pageLast">4278</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC200300072.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="5"></count><count type="tableTotal" number="0"></count><count type="referenceTotal" number="15"></count></countGroup><titleGroup><title type="main" xml:lang="en">Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by <i>N</i>‐Acylhydrazonium Ion Aromatic π‐Cyclization</title><title type="short" xml:lang="en">Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Alain</givenNames><familyName>Fogain‐Ninkam</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Adam</givenNames><familyName>Daïch</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Bernard</givenNames><familyName>Decroix</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Pierre</givenNames><familyName>Netchitaïlo</familyName></personName><contactDetails><email normalForm="pierre.netchitailo@univ-lehavre.fr">pierre.netchitailo@univ‐lehavre.fr</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="FR" type="organization"><unparsedAffiliation>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Alkaloids</keyword><keyword xml:id="kwd2">Cyclization</keyword><keyword xml:id="kwd3">Nitrogen heterocycles</keyword><keyword xml:id="kwd4">Reduction</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Hydroxylactams <b>6a</b>−<b>c</b> and <b>7a</b>−<b>c</b> were synthesized by successive regioselective reductions of arylideneaminophthalimides <b>3a</b>−<b>c</b>, which were easily available from aminophthalimide <b>1</b> and benzaldehyde (<b>2a</b>) or thiophenecarboxaldehydes <b>2b</b> and <b>2c</b>. <i>N</i>‐Acylhydrazonium ions <b>III</b>, generated in the presence of Lewis acid from acetoxy derivatives <b>8a</b> and <b>9a</b> of hydroxylactams <b>6a</b> and <b>7a</b>, or in organic acid medium directly from hydroxylactams <b>6b</b> and <b>6c</b>, induced the expected isoindolo‐phthalazines <b>10a</b> and <b>11a</b> and thienopyridazino‐isoindolones <b>12b</b> and <b>12c</b>. On the other hand, hydroxylactams <b>7b</b> and <b>7c</b> under acidic conditions gave the unexpected <i>N</i>‐thienylmethyl‐substituted thienopyridazino‐isoindolones <b>13b</b> and<b> 13c</b>. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization</title></titleInfo><name type="personal"><namePart type="given">Alain</namePart><namePart type="family">Fogain‐Ninkam</namePart><affiliation>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Adam</namePart><namePart type="family">Daïch</namePart><affiliation>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bernard</namePart><namePart type="family">Decroix</namePart><affiliation>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Pierre</namePart><namePart type="family">Netchitaïlo</namePart><affiliation>Université du Havre, URCOM, EA 3221, UFR des Sciences et Techniques 25 Rue Philippe Lebon, BP540, 76058 Le Havre Cedex, France, Fax: (internat.) + 33‐2‐32744391</affiliation><affiliation>E-mail: pierre.netchitailo@univ‐lehavre.fr</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article"></genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2003-11</dateIssued><dateCaptured encoding="w3cdtf">2003-02-06</dateCaptured><copyrightDate encoding="w3cdtf">2003</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">5</extent><extent unit="references">15</extent></physicalDescription><abstract>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</abstract><subject lang="en"><genre>keywords</genre><topic>Alkaloids</topic><topic>Cyclization</topic><topic>Nitrogen heterocycles</topic><topic>Reduction</topic></subject><relatedItem type="host"><titleInfo><title>European Journal of Organic Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>Eur. J. Org. Chem.</title></titleInfo><genre type="journal">journal</genre><subject><genre>article-category</genre><topic>Full Paper</topic></subject><identifier type="ISSN">1434-193X</identifier><identifier type="eISSN">1099-0690</identifier><identifier type="DOI">10.1002/(ISSN)1099-0690</identifier><identifier type="PublisherID">EJOC</identifier><part><date>2003</date><detail type="volume"><caption>vol.</caption><number>2003</number></detail><detail type="issue"><caption>no.</caption><number>21</number></detail><extent unit="pages"><start>4273</start><end>4278</end><total>7</total></extent></part></relatedItem><identifier type="istex">6A018384956A55AEAE822799E4A059255DEFAED3</identifier><identifier type="DOI">10.1002/ejoc.200300072</identifier><identifier type="ArticleID">EJOC200300072</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. 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