Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches
Identifieur interne : 000F11 ( Istex/Corpus ); précédent : 000F10; suivant : 000F12Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches
Auteurs : Nicolas Brosse ; Maria-Fatima Pinto ; Brigitte Jamart-GrégoireSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2003-12.
English descriptors
- KwdEn :
- Acidic, Acidic partners, Alkyl, Alkylation, Alkylhydrazine derivatives, Brosse, Calcd, Catalytic amount, Cdcl3, Ch2ph, Chem, Derivative, Diethyl, Diethyl ether, Ester, Ether, Full paper, General procedure, Gmbh, Hrms, Hrms calcd, Hydrazine, Hydrazine derivatives, Hydrazino esters, Kgaa, Methylamine, Mitsunobu, Mitsunobu approach, Mitsunobu reaction, Mmol, Obzl, Otbu, Phthaloyl, Phthaloyl group, Pinto, Room temperature, Secondary alkyl groups, Steric hindrance, Vacuo, Verlag, Verlag gmbh, Weinheim.
- Teeft :
- Acidic, Acidic partners, Alkyl, Alkylation, Alkylhydrazine derivatives, Brosse, Calcd, Catalytic amount, Cdcl3, Ch2ph, Chem, Derivative, Diethyl, Diethyl ether, Ester, Ether, Full paper, General procedure, Gmbh, Hrms, Hrms calcd, Hydrazine, Hydrazine derivatives, Hydrazino esters, Kgaa, Methylamine, Mitsunobu, Mitsunobu approach, Mitsunobu reaction, Mmol, Obzl, Otbu, Phthaloyl, Phthaloyl group, Pinto, Room temperature, Secondary alkyl groups, Steric hindrance, Vacuo, Verlag, Verlag gmbh, Weinheim.
Abstract
Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N‐aminophthalimide derivatives can be efficiently converted into the corresponding N‐amino‐imidodicarbonates by a three‐stage, one‐flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ‐diprotected α‐hydrazino esters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Url:
DOI: 10.1002/ejoc.200300445
Links to Exploration step
ISTEX:2A157FD93633C65700766D42CE92A1DC135A2A4CLe document en format XML
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It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N‐aminophthalimide derivatives can be efficiently converted into the corresponding N‐amino‐imidodicarbonates by a three‐stage, one‐flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ‐diprotected α‐hydrazino esters. (© Wiley‐VCH Verlag GmbH & Co. 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It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc<hi rend="subscript">2</hi>) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, <hi rend="italic">N</hi>‐aminophthalimide derivatives can be efficiently converted into the corresponding <hi rend="italic">N</hi>‐amino‐imidodicarbonates by a three‐stage, one‐flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally <hi rend="italic">N</hi><hi rend="superscript">α</hi><hi rend="italic">,N</hi><hi rend="superscript">β</hi>‐diprotected α‐hydrazino esters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">Hydrazine derivatives</term><term xml:id="kwd2">Phase‐transfer catalysis</term><term xml:id="kwd3">Mitsunobu reaction</term><term xml:id="kwd4">α‐Hydrazino acids</term><term xml:id="kwd5">Protecting groups</term></keywords><keywords rend="articleCategory"><term>Full Paper</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/2A157FD93633C65700766D42CE92A1DC135A2A4C/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. J. Org. Chem.</title></titleGroup></publicationMeta><publicationMeta level="part" position="240"><doi origin="wiley" registered="yes">10.1002/ejoc.v2003:24</doi><numberingGroup><numbering type="journalVolume" number="2003">2003</numbering><numbering type="journalIssue">24</numbering></numberingGroup><coverDate startDate="2003-12">December 2003</coverDate></publicationMeta><publicationMeta level="unit" type="article" position="13" status="forIssue"><doi origin="wiley" registered="yes">10.1002/ejoc.200300445</doi><idGroup><id type="unit" value="EJOC200300445"></id></idGroup><countGroup><count type="pageTotal" number="8"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title></titleGroup><copyright ownership="publisher">Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2003-07-17"></event><event type="firstOnline" date="2003-12-04"></event><event type="publishedOnlineFinalForm" date="2003-12-04"></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">4757</numbering><numbering type="pageLast">4764</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC200300445.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="4"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="9"></count></countGroup><titleGroup><title type="main" xml:lang="en">Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches</title><title type="short" xml:lang="en">Preparation of Multiply Protected Alkylhydrazine Derivatives</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Nicolas</givenNames><familyName>Brosse</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Maria‐Fatima</givenNames><familyName>Pinto</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Brigitte</givenNames><familyName>Jamart‐Grégoire</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="FR" type="organization"><unparsedAffiliation>Laboratoire de Chimie‐Physique Macromoléculaire (LCPM), UMR CNRS‐INPL 7568, ENSIC, BP 451, 54001 Nancy Cedex, France Fax: (internat.) + 33‐383‐379977</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Hydrazine derivatives</keyword><keyword xml:id="kwd2">Phase‐transfer catalysis</keyword><keyword xml:id="kwd3">Mitsunobu reaction</keyword><keyword xml:id="kwd4">α‐Hydrazino acids</keyword><keyword xml:id="kwd5">Protecting groups</keyword></keywordGroup><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc<sub>2</sub>) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, <i>N</i>‐aminophthalimide derivatives can be efficiently converted into the corresponding <i>N</i>‐amino‐imidodicarbonates by a three‐stage, one‐flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally <i>N</i><sup>α</sup><i>,N</i><sup>β</sup>‐diprotected α‐hydrazino esters. (© 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>Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Preparation of Multiply Protected Alkylhydrazine Derivatives</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches</title></titleInfo><name type="personal"><namePart type="given">Nicolas</namePart><namePart type="family">Brosse</namePart><affiliation>Laboratoire de Chimie‐Physique Macromoléculaire (LCPM), UMR CNRS‐INPL 7568, ENSIC, BP 451, 54001 Nancy Cedex, France Fax: (internat.) + 33‐383‐379977</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Maria‐Fatima</namePart><namePart type="family">Pinto</namePart><affiliation>Laboratoire de Chimie‐Physique Macromoléculaire (LCPM), UMR CNRS‐INPL 7568, ENSIC, BP 451, 54001 Nancy Cedex, France Fax: (internat.) + 33‐383‐379977</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Brigitte</namePart><namePart type="family">Jamart‐Grégoire</namePart><affiliation>Laboratoire de Chimie‐Physique Macromoléculaire (LCPM), UMR CNRS‐INPL 7568, ENSIC, BP 451, 54001 Nancy Cedex, France Fax: (internat.) + 33‐383‐379977</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2003-12</dateIssued><dateCaptured encoding="w3cdtf">2003-07-17</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><extent unit="figures">4</extent><extent unit="tables">1</extent><extent unit="references">9</extent></physicalDescription><abstract lang="en">Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N‐aminophthalimide derivatives can be efficiently converted into the corresponding N‐amino‐imidodicarbonates by a three‐stage, one‐flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ‐diprotected α‐hydrazino esters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</abstract><subject lang="en"><genre>keywords</genre><topic>Hydrazine derivatives</topic><topic>Phase‐transfer catalysis</topic><topic>Mitsunobu reaction</topic><topic>α‐Hydrazino acids</topic><topic>Protecting groups</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" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">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>24</number></detail><extent unit="pages"><start>4757</start><end>4764</end><total>8</total></extent></part></relatedItem><identifier type="istex">2A157FD93633C65700766D42CE92A1DC135A2A4C</identifier><identifier type="ark">ark:/67375/WNG-ZS8NTXQ1-L</identifier><identifier type="DOI">10.1002/ejoc.200300445</identifier><identifier type="ArticleID">EJOC200300445</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. 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