Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization
Identifieur interne : 000537 ( Istex/Corpus ); précédent : 000536; suivant : 000538Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization
Auteurs : Armelle Cul ; Anthony Pesquet ; Adam Daïch ; Abderrahim Chihab-Eddine ; Štefan MarchalínSource :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 2003-05.
Abstract
Fused isoindolo[1,3]benzo(or thieno)oxazepines 8a,b and one of their positional isomers aromatic tricyclic N,O‐acetals 13b are reported to occur efficiently in a three‐step sequence from N‐hydroxy‐methylphthalimide (6). The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic N‐acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam 13b, is discussed.
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DOI: 10.1002/jhet.5570400314
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type="organization"><unparsedAffiliation>Laboratoire de Bio‐Organique, Département de Chimie, Faculté des Sciences, Université Ibnou Zohr, B.P:28/S, Agadir, Maroc</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="SK" type="organization"><unparsedAffiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK‐812 37 Bratislava, Slovakia</unparsedAffiliation></affiliation></affiliationGroup><fundingInfo><fundingAgency>Scientific Council of University of Le Havre</fundingAgency></fundingInfo><fundingInfo><fundingAgency>Slovak</fundingAgency><fundingNumber>1/9249/2002</fundingNumber></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Fused isoindolo[1,3]benzo(or thieno)oxazepines <b>8a,b</b> and one of their positional isomers aromatic tricyclic <i>N,O</i>‐acetals <b>13b</b> are reported to occur efficiently in a three‐step sequence from <i>N</i>‐hydroxy‐methylphthalimide <b>(6)</b>. The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic <i>N</i>‐acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam <b>13b</b>, is discussed.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Evaluation of N‐Hydroxymethylphthalimide in Alkaline Medium</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization</title></titleInfo><name type="personal"><namePart type="given">Armelle</namePart><namePart type="family">Cul</namePart><affiliation>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Anthony</namePart><namePart type="family">Pesquet</namePart><affiliation>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Adam</namePart><namePart type="family">Daïch</namePart><affiliation>Laboratoire de Chimie, URCOM, EA 3221, Faculté des Sciences & Techniques de l'Université du Havre, B.P: 540, 25 Rue Philippe Lebon, F‐76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Abderrahim</namePart><namePart type="family">Chihab‐Eddine</namePart><affiliation>Laboratoire de Bio‐Organique, Département de Chimie, Faculté des Sciences, Université Ibnou Zohr, B.P:28/S, Agadir, Maroc</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Štefan</namePart><namePart type="family">Marchalín</namePart><affiliation>Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK‐812 37 Bratislava, Slovakia</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article"></genre><originInfo><publisher>Wiley‐Blackwell</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2003-05</dateIssued><dateCaptured encoding="w3cdtf">2003-02-20</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="tables">1</extent><extent unit="references">30</extent></physicalDescription><abstract>Fused isoindolo[1,3]benzo(or thieno)oxazepines 8a,b and one of their positional isomers aromatic tricyclic N,O‐acetals 13b are reported to occur efficiently in a three‐step sequence from N‐hydroxy‐methylphthalimide (6). The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic N‐acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam 13b, is discussed.</abstract><note type="funding">Scientific Council of University of Le Havre</note><note type="funding">Slovak - No. 1/9249/2002; </note><relatedItem type="host"><titleInfo><title>Journal of Heterocyclic Chemistry</title></titleInfo><genre type="journal">journal</genre><subject><genre>article-category</genre><topic>Article</topic></subject><identifier type="ISSN">0022-152X</identifier><identifier type="eISSN">1943-5193</identifier><identifier type="DOI">10.1002/(ISSN)1943-5193</identifier><identifier type="PublisherID">JHET</identifier><part><date>2003</date><detail type="volume"><caption>vol.</caption><number>40</number></detail><detail type="issue"><caption>no.</caption><number>3</number></detail><extent unit="pages"><start>499</start><end>505</end><total>7</total></extent></part></relatedItem><identifier type="istex">7BEF34D898D7FD27B9C36C9CE81F80E3FB784F64</identifier><identifier type="DOI">10.1002/jhet.5570400314</identifier><identifier type="ArticleID">JHET5570400314</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2003 Journal of Heterocyclic Chemistry</accessCondition><recordInfo><recordContentSource>WILEY</recordContentSource><recordOrigin>Wiley‐Blackwell</recordOrigin></recordInfo></mods></metadata><enrichments><json:item><type>multicat</type><uri>https://api.istex.fr/document/7BEF34D898D7FD27B9C36C9CE81F80E3FB784F64/enrichments/multicat</uri></json:item></enrichments><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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