Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization
Identifieur interne : 000327 ( Istex/Corpus ); précédent : 000326; suivant : 000328Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization
Auteurs : Abderrahim Chihab-Eddine ; Adam Da Ch ; Abderrahim Jilale ; Bernard DecroixSource :
- Tetrahedron Letters [ 0040-4039 ] ; 2001.
English descriptors
Abstract
Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.
Url:
DOI: 10.1016/S0040-4039(00)02037-2
Links to Exploration step
ISTEX:55267173D7D79235E9192CC60B7433A2169AE796Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title><author><name sortKey="Chihab Eddine, Abderrahim" sort="Chihab Eddine, Abderrahim" uniqKey="Chihab Eddine A" first="Abderrahim" last="Chihab-Eddine">Abderrahim Chihab-Eddine</name><affiliation><mods:affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</mods:affiliation></affiliation></author><author><name sortKey="Da Ch, Adam" sort="Da Ch, Adam" uniqKey="Da Ch A" first="Adam" last="Da Ch">Adam Da Ch</name><affiliation><mods:affiliation>E-mail: adam.daich@univ-lehavre.fr</mods:affiliation></affiliation><affiliation><mods:affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Jilale, Abderrahim" sort="Jilale, Abderrahim" uniqKey="Jilale A" first="Abderrahim" last="Jilale">Abderrahim Jilale</name><affiliation><mods:affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</mods:affiliation></affiliation></author><author><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><affiliation><mods:affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:55267173D7D79235E9192CC60B7433A2169AE796</idno><date when="2001" year="2001">2001</date><idno type="doi">10.1016/S0040-4039(00)02037-2</idno><idno type="url">https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">000327</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title><author><name sortKey="Chihab Eddine, Abderrahim" sort="Chihab Eddine, Abderrahim" uniqKey="Chihab Eddine A" first="Abderrahim" last="Chihab-Eddine">Abderrahim Chihab-Eddine</name><affiliation><mods:affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</mods:affiliation></affiliation></author><author><name sortKey="Da Ch, Adam" sort="Da Ch, Adam" uniqKey="Da Ch A" first="Adam" last="Da Ch">Adam Da Ch</name><affiliation><mods:affiliation>E-mail: adam.daich@univ-lehavre.fr</mods:affiliation></affiliation><affiliation><mods:affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Jilale, Abderrahim" sort="Jilale, Abderrahim" uniqKey="Jilale A" first="Abderrahim" last="Jilale">Abderrahim Jilale</name><affiliation><mods:affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</mods:affiliation></affiliation></author><author><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name><affiliation><mods:affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</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="2001">2001</date><biblScope unit="volume">42</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="573">573</biblScope><biblScope unit="page" to="576">576</biblScope></imprint><idno type="ISSN">0040-4039</idno></series><idno type="istex">55267173D7D79235E9192CC60B7433A2169AE796</idno><idno type="DOI">10.1016/S0040-4039(00)02037-2</idno><idno type="PII">S0040-4039(00)02037-2</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4039</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>N-acyliminium ion</term><term>aza-compounds</term><term>benzo[d]thiepine</term><term>isothiochroman</term><term>π-cationic cyclization</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.</div></front></TEI><istex><corpusName>elsevier</corpusName><author><json:item><name>Abderrahim Chihab-Eddine</name><affiliations><json:string>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</json:string></affiliations></json:item><json:item><name>Adam Daı̈ch</name><affiliations><json:string>E-mail: adam.daich@univ-lehavre.fr</json:string><json:string>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</json:string></affiliations></json:item><json:item><name>Abderrahim Jilale</name><affiliations><json:string>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</json:string></affiliations></json:item><json:item><name>Bernard Decroix</name><affiliations><json:string>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>N-acyliminium ion</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>π-cationic cyclization</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>aza-compounds</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>isothiochroman</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>benzo[d]thiepine</value></json:item></subject><language><json:string>eng</json:string></language><originalGenre><json:string>Short communication</json:string></originalGenre><abstract>Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.</abstract><qualityIndicators><score>2.236</score><pdfVersion>1.2</pdfVersion><pdfPageSize>594 x 780 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>5</keywordCount><abstractCharCount>352</abstractCharCount><pdfWordCount>1732</pdfWordCount><pdfCharCount>11104</pdfCharCount><pdfPageCount>4</pdfPageCount><abstractWordCount>42</abstractWordCount></qualityIndicators><title>Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title><pii><json:string>S0040-4039(00)02037-2</json:string></pii><genre><json:string>brief-communication</json:string></genre><host><volume>42</volume><pii><json:string>S0040-4039(00)X0528-X</json:string></pii><pages><last>576</last><first>573</first></pages><issn><json:string>0040-4039</json:string></issn><issue>4</issue><genre><json:string>journal</json:string></genre><language><json:string>unknown</json:string></language><title>Tetrahedron Letters</title><publicationDate>2001</publicationDate></host><categories><wos><json:string>CHEMISTRY, ORGANIC</json:string></wos></categories><publicationDate>2001</publicationDate><copyrightDate>2001</copyrightDate><doi><json:string>10.1016/S0040-4039(00)02037-2</json:string></doi><id>55267173D7D79235E9192CC60B7433A2169AE796</id><score>0.45750773</score><fulltext><json:item><original>true</original><mimetype>application/pdf</mimetype><extension>pdf</extension><uri>https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/fulltext/pdf</uri></json:item><json:item><original>false</original><mimetype>application/zip</mimetype><extension>zip</extension><uri>https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>©2001 Elsevier Science Ltd</p></availability><date>2001</date></publicationStmt><notesStmt><note type="content">Scheme 1:</note><note type="content">Scheme 2: Reagents: (i) 1 equiv. of (S)-MeCH(CH2)Ph, CH2Cl2, 0°C then 16 h at rt; (ii) 1 equiv. of (COCl)2, 1 drop of DMF, 8 h at rt; (iii) 1 equiv. of NEt3, CH2Cl2, 1 h at rt; (iv) 1 equiv. of (S)-MeCH(NH2)Ph, xylene, 12 h at reflux.</note><note type="content">Scheme 3: Reagents: (i) 6 equiv. of NaBH4, methanol, 0–5°C, 30 min; (ii) R1-CC-Li, Et2O, 0–25°C, 3 h; (iii) PTSA, ethanol, reflux, 2 h; (iv) R2-MgX, see Table 1 for reaction conditions.</note><note type="content">Scheme 4: Reagents: (i) 1–1.2 equiv. of MeONa, 1–1.2 equiv. of R2SH, C6H6, 40–60°C, 12 h; (ii) NaBH4, MeOH, 0–5°C, 30 min.</note><note type="content">Table 1: Grignard reagent addition onto Michael acceptor enone 5; derivatives 9 and 10 produced via Scheme 3</note></notesStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title><author xml:id="author-1"><persName><forename type="first">Abderrahim</forename><surname>Chihab-Eddine</surname></persName><affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</affiliation></author><author xml:id="author-2"><persName><forename type="first">Adam</forename><surname>Daı̈ch</surname></persName><email>adam.daich@univ-lehavre.fr</email><note type="correspondence"><p>Corresponding author. Tel.: (+33) 02-32-74-44-03; fax: (+33) 02-32-74-43-91</p></note><affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</affiliation></author><author xml:id="author-3"><persName><forename type="first">Abderrahim</forename><surname>Jilale</surname></persName><affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</affiliation></author><author xml:id="author-4"><persName><forename type="first">Bernard</forename><surname>Decroix</surname></persName><affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</affiliation></author></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)X0528-X</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="2001"></date><biblScope unit="volume">42</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="573">573</biblScope><biblScope unit="page" to="576">576</biblScope></imprint></monogr><idno type="istex">55267173D7D79235E9192CC60B7433A2169AE796</idno><idno type="DOI">10.1016/S0040-4039(00)02037-2</idno><idno type="PII">S0040-4039(00)02037-2</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>2001</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.</p></abstract><abstract style="graphical"><p>Graphicloc1</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>Keywords</head><item><term>N-acyliminium ion</term></item><item><term>π-cationic cyclization</term></item><item><term>aza-compounds</term></item><item><term>isothiochroman</term></item><item><term>benzo[d]thiepine</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2001">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><original>false</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: ce:floats; body; 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="loc1" NDATA="IMAGE" name="loc1"></istex:entity><istex:entity SYSTEM="sc1" NDATA="IMAGE" name="sc1"></istex:entity><istex:entity SYSTEM="sc2" NDATA="IMAGE" name="sc2"></istex:entity><istex:entity SYSTEM="sc3" NDATA="IMAGE" name="sc3"></istex:entity><istex:entity SYSTEM="sc4" NDATA="IMAGE" name="sc4"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="sco" xml:lang="en"><item-info><jid>TETL</jid><aid>18310</aid><ce:pii>S0040-4039(00)02037-2</ce:pii><ce:doi>10.1016/S0040-4039(00)02037-2</ce:doi><ce:copyright type="full-transfer" year="2001">Elsevier Science Ltd</ce:copyright></item-info><head><ce:title>Synthesis and reactivity of (1<ce:italic>S</ce:italic>)-<ce:italic>N</ce:italic>-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[<ce:italic>d</ce:italic>]thiepine based on π-cationic cyclization</ce:title><ce:author-group><ce:author><ce:given-name>Abderrahim</ce:given-name><ce:surname>Chihab-Eddine</ce:surname><ce:cross-ref refid="AFF1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Adam</ce:given-name><ce:surname>Daı̈ch</ce:surname><ce:cross-ref refid="AFF2"><ce:sup>b</ce:sup></ce:cross-ref><ce:cross-ref refid="COR1">*</ce:cross-ref><ce:e-address type="email">adam.daich@univ-lehavre.fr</ce:e-address></ce:author><ce:author><ce:given-name>Abderrahim</ce:given-name><ce:surname>Jilale</ce:surname><ce:cross-ref refid="AFF1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Bernard</ce:given-name><ce:surname>Decroix</ce:surname><ce:cross-ref refid="AFF2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:affiliation id="AFF1"><ce:label>a</ce:label><ce:textfn>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</ce:textfn></ce:affiliation><ce:affiliation id="AFF2"><ce:label>b</ce:label><ce:textfn>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</ce:textfn></ce:affiliation><ce:correspondence id="COR1"><ce:label>*</ce:label><ce:text>Corresponding author. Tel.: (+33) 02-32-74-44-03; fax: (+33) 02-32-74-43-91</ce:text></ce:correspondence></ce:author-group><ce:date-received day="14" month="10" year="2000"></ce:date-received><ce:date-accepted day="9" month="11" year="2000"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>Chiral pyrroloisothiochroman and pyrrolo[<ce:italic>d</ce:italic>]thiepine were obtained efficiently in four steps from <ce:italic>N</ce:italic>-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the <ce:italic>N</ce:italic>-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>Graphic</ce:simple-para></ce:abstract-sec><ce:figure><ce:link locator="loc1"></ce:link></ce:figure></ce:abstract><ce:keywords class="keyword"><ce:section-title>Keywords</ce:section-title><ce:keyword><ce:text><ce:italic>N</ce:italic>-acyliminium ion</ce:text></ce:keyword><ce:keyword><ce:text>π-cationic cyclization</ce:text></ce:keyword><ce:keyword><ce:text>aza-compounds</ce:text></ce:keyword><ce:keyword><ce:text>isothiochroman</ce:text></ce:keyword><ce:keyword><ce:text>benzo[<ce:italic>d</ce:italic>]thiepine</ce:text></ce:keyword></ce:keywords></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Synthesis and reactivity of (1</title></titleInfo><name type="personal"><namePart type="given">Abderrahim</namePart><namePart type="family">Chihab-Eddine</namePart><affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Adam</namePart><namePart type="family">Daı̈ch</namePart><affiliation>E-mail: adam.daich@univ-lehavre.fr</affiliation><affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</affiliation><description>Corresponding author. Tel.: (+33) 02-32-74-44-03; fax: (+33) 02-32-74-43-91</description><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Abderrahim</namePart><namePart type="family">Jilale</namePart><affiliation>Laboratoire de Bio-Organique, Département de Chimie, Université Ibnou Zohr, Faculté des Sciences, B.P. 28/S, Agadir, Morocco</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bernard</namePart><namePart type="family">Decroix</namePart><affiliation>Laboratoire de Chimie, URCOM, Faculté des Sciences & Techniques de l'Université du Havre, 25 rue Philippe Lebon, B.P. 540, 76058 Le Havre Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="Short communication"></genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">2001</dateIssued><copyrightDate encoding="w3cdtf">2001</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="en">Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.</abstract><abstract type="graphical">Graphicloc1 </abstract><note type="content">Scheme 1: </note><note type="content">Scheme 2: Reagents: (i) 1 equiv. of (S)-MeCH(CH2)Ph, CH2Cl2, 0°C then 16 h at rt; (ii) 1 equiv. of (COCl)2, 1 drop of DMF, 8 h at rt; (iii) 1 equiv. of NEt3, CH2Cl2, 1 h at rt; (iv) 1 equiv. of (S)-MeCH(NH2)Ph, xylene, 12 h at reflux.</note><note type="content">Scheme 3: Reagents: (i) 6 equiv. of NaBH4, methanol, 0–5°C, 30 min; (ii) R1-CC-Li, Et2O, 0–25°C, 3 h; (iii) PTSA, ethanol, reflux, 2 h; (iv) R2-MgX, see Table 1 for reaction conditions.</note><note type="content">Scheme 4: Reagents: (i) 1–1.2 equiv. of MeONa, 1–1.2 equiv. of R2SH, C6H6, 40–60°C, 12 h; (ii) NaBH4, MeOH, 0–5°C, 30 min.</note><note type="content">Table 1: Grignard reagent addition onto Michael acceptor enone 5; derivatives 9 and 10 produced via Scheme 3</note><subject lang="en"><genre>Keywords</genre><topic>N-acyliminium ion</topic><topic>π-cationic cyclization</topic><topic>aza-compounds</topic><topic>isothiochroman</topic><topic>benzo[d]thiepine</topic></subject><relatedItem type="host"><titleInfo><title>Tetrahedron Letters</title></titleInfo><titleInfo type="abbreviated"><title>TETL</title></titleInfo><genre type="journal">journal</genre><originInfo><dateIssued encoding="w3cdtf">20010122</dateIssued></originInfo><identifier type="ISSN">0040-4039</identifier><identifier type="PII">S0040-4039(00)X0528-X</identifier><part><date>20010122</date><detail type="volume"><number>42</number><caption>vol.</caption></detail><detail type="issue"><number>4</number><caption>no.</caption></detail><extent unit="issue pages"><start>539</start><end>768</end></extent><extent unit="pages"><start>573</start><end>576</end></extent></part></relatedItem><identifier type="istex">55267173D7D79235E9192CC60B7433A2169AE796</identifier><identifier type="DOI">10.1016/S0040-4039(00)02037-2</identifier><identifier type="PII">S0040-4039(00)02037-2</identifier><accessCondition type="use and reproduction" contentType="copyright">©2001 Elsevier Science Ltd</accessCondition><recordInfo><recordContentSource>ELSEVIER</recordContentSource><recordOrigin>Elsevier Science Ltd, ©2001</recordOrigin></recordInfo></mods></metadata><enrichments><istex:catWosTEI uri="https://api.istex.fr/document/55267173D7D79235E9192CC60B7433A2169AE796/enrichments/catWos"><teiHeader><profileDesc><textClass><classCode scheme="WOS">CHEMISTRY, ORGANIC</classCode></textClass></profileDesc></teiHeader></istex:catWosTEI></enrichments><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/France/explor/LeHavreV1/Data/Istex/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000327 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Istex/Corpus/biblio.hfd -nk 000327 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/France
|area= LeHavreV1
|flux= Istex
|étape= Corpus
|type= RBID
|clé= ISTEX:55267173D7D79235E9192CC60B7433A2169AE796
|texte= Synthesis and reactivity of (1 S )- N -(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d ]thiepine based on π-cationic cyclization
}}
| This area was generated with Dilib version V0.6.25. |  |