<?xml version="1.0" encoding="utf-8"?>
<TEI xmlns="http://www.tei-c.org/ns/1.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:hal="http://hal.archives-ouvertes.fr/" xmlns:gml="http://www.opengis.net/gml/3.3/" xmlns:gmlce="http://www.opengis.net/gml/3.3/ce" version="1.1" xsi:schemaLocation="http://www.tei-c.org/ns/1.0 http://api.archives-ouvertes.fr/documents/aofr-sword.xsd">
  <teiHeader>
    <fileDesc>
      <titleStmt>
        <title>HAL TEI export of hal-03274724</title>
      </titleStmt>
      <publicationStmt>
        <distributor>CCSD</distributor>
        <availability status="restricted">
          <licence target="https://creativecommons.org/publicdomain/zero/1.0/">CC0 1.0 - Universal</licence>
        </availability>
        <date when="2026-05-16T14:25:09+02:00"/>
      </publicationStmt>
      <sourceDesc>
        <p part="N">HAL API Platform</p>
      </sourceDesc>
    </fileDesc>
  </teiHeader>
  <text>
    <body>
      <listBibl>
        <biblFull>
          <titleStmt>
            <title xml:lang="en">Aminations and arylations by direct C–O activation for the design of 7,8-dihydro-6H -5,8-ethanopyrido[3,2- d]pyrimidines</title>
            <author role="aut">
              <persName>
                <forename type="first">Mazarine</forename>
                <surname>Laurent</surname>
              </persName>
              <idno type="halauthorid">2240494-0</idno>
              <affiliation ref="#struct-199928"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Stéphane</forename>
                <surname>Bostyn</surname>
              </persName>
              <idno type="idhal" notation="numeric">773070</idno>
              <idno type="halauthorid" notation="string">884016-773070</idno>
              <idno type="ORCID">https://orcid.org/0000-0002-0313-9150</idno>
              <affiliation ref="#struct-474628"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Mathieu</forename>
                <surname>Marchivie</surname>
              </persName>
              <email type="md5">bbd5e0d094d38acb84d5ee7b5cbc2c00</email>
              <email type="domain">icmcb.cnrs.fr</email>
              <idno type="idhal" notation="string">mathieu-marchivie</idno>
              <idno type="idhal" notation="numeric">735720</idno>
              <idno type="halauthorid" notation="string">41834-735720</idno>
              <idno type="IDREF">https://www.idref.fr/077034007</idno>
              <idno type="ORCID">https://orcid.org/0000-0003-1362-0797</idno>
              <idno type="VIAF">https://viaf.org/viaf/199905850</idno>
              <idno type="ISNI">http://isni.org/isni/0000000357713960</idno>
              <affiliation ref="#struct-525101"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Yves</forename>
                <surname>Robin</surname>
              </persName>
              <idno type="halauthorid">145334-0</idno>
              <affiliation ref="#struct-1072592"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Sylvain</forename>
                <surname>Routier</surname>
              </persName>
              <email type="md5">02224a195402ffd13bdaec52362e2046</email>
              <email type="domain">univ-orleans.fr</email>
              <idno type="idhal" notation="string">sylvain-routier</idno>
              <idno type="idhal" notation="numeric">936554</idno>
              <idno type="halauthorid" notation="string">225531-936554</idno>
              <idno type="IDREF">https://www.idref.fr/118636367</idno>
              <idno type="ISNI">http://isni.org/isni/0000000430819818</idno>
              <idno type="VIAF">https://viaf.org/viaf/173427768</idno>
              <idno type="ORCID">https://orcid.org/0000-0002-2823-0591</idno>
              <affiliation ref="#struct-199928"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Frédéric</forename>
                <surname>Buron</surname>
              </persName>
              <email type="md5">9351b841c7c765a0f707d1039576fb6a</email>
              <email type="domain">univ-orleans.fr</email>
              <idno type="idhal" notation="string">frederic-buron</idno>
              <idno type="idhal" notation="numeric">1103789</idno>
              <idno type="halauthorid" notation="string">499611-1103789</idno>
              <idno type="ORCID">https://orcid.org/0000-0001-5773-1515</idno>
              <idno type="GOOGLE SCHOLAR">https://scholar.google.fr/citations?user=Q_4mAo4AAAAJ</idno>
              <affiliation ref="#struct-199928"/>
            </author>
            <editor role="depositor">
              <persName>
                <forename>Stéphane</forename>
                <surname>Toulin</surname>
              </persName>
              <email type="md5">f3db7e37777e25f87d33a6d60b9d9a3e</email>
              <email type="domain">icmcb.cnrs.fr</email>
            </editor>
            <funder ref="#projanr-25520"/>
            <funder ref="#projanr-26984"/>
            <funder>The authors would like to thank the Région Centre Val de Loire (RTR Motivhealth, APR-IR FLOWSYN and INFLUX), FEDER under projects Valbiocosm FEDER-FSE 2017-EX003202, CHembio FEDER-FSE 2014-2020-EX003677, Techsab FEDER-FSE 2014-2020-EX011313 and Mistic FEDER-FSE 2014-2020-EX003242; the SFR neuroimagerie (SFR FED 4224), the GDR Synth_Flux, the Labex programs SYNORG (ANR-11-LABX-0029) and IRON (ANR-11-LABX-0018-01), the Ligue contre le Cancer du Grand Ouest (comités des Deux Sèvres, du Finistère, de l’Ile et Villaine, du Loir et Cher, de Loire Atlantique, du Loiret, de la Vienne) for their financial support.</funder>
          </titleStmt>
          <editionStmt>
            <edition n="v1" type="current">
              <date type="whenSubmitted">2021-06-30 13:40:44</date>
              <date type="whenModified">2026-03-26 08:50:02</date>
              <date type="whenReleased">2021-07-06 07:51:25</date>
              <date type="whenProduced">2021-05-28</date>
              <date type="whenEndEmbargoed">2021-06-30</date>
              <ref type="file" target="https://hal.science/hal-03274724v1/document">
                <date notBefore="2021-06-30"/>
              </ref>
              <ref type="file" subtype="publisherPaid" n="1" target="https://hal.science/hal-03274724v1/file/2021-092.pdf" id="file-3274724-2877386">
                <date notBefore="2021-06-30"/>
              </ref>
              <ref type="externalLink" target="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033610"/>
            </edition>
            <respStmt>
              <resp>contributor</resp>
              <name key="101680">
                <persName>
                  <forename>Stéphane</forename>
                  <surname>Toulin</surname>
                </persName>
                <email type="md5">f3db7e37777e25f87d33a6d60b9d9a3e</email>
                <email type="domain">icmcb.cnrs.fr</email>
              </name>
            </respStmt>
          </editionStmt>
          <publicationStmt>
            <distributor>CCSD</distributor>
            <idno type="halId">hal-03274724</idno>
            <idno type="halUri">https://hal.science/hal-03274724</idno>
            <idno type="halBibtex">laurent:hal-03274724</idno>
            <idno type="halRefHtml">&lt;i&gt;RSC Advances&lt;/i&gt;, 2021, 11 (32), pp.19363-19377. &lt;a target="_blank" href="https://dx.doi.org/10.1039/D1RA03092B"&gt;&amp;#x27E8;10.1039/D1RA03092B&amp;#x27E9;&lt;/a&gt;</idno>
            <idno type="halRef">RSC Advances, 2021, 11 (32), pp.19363-19377. &amp;#x27E8;10.1039/D1RA03092B&amp;#x27E9;</idno>
            <availability status="restricted">
              <licence target="https://about.hal.science/hal-authorisation-v1/">HAL Authorization<ref corresp="#file-3274724-2877386"/></licence>
            </availability>
          </publicationStmt>
          <seriesStmt>
            <idno type="stamp" n="INSERM">INSERM - Institut national de la santé et de la recherche médicale</idno>
            <idno type="stamp" n="CEA">CEA - Commissariat à l'énergie atomique</idno>
            <idno type="stamp" n="CNRS">CNRS - Centre national de la recherche scientifique</idno>
            <idno type="stamp" n="UNIV-ORLEANS">Université d'Orléans</idno>
            <idno type="stamp" n="ICMCB">Institut de chimie de la matière condensée de Bordeaux</idno>
            <idno type="stamp" n="ICOA" corresp="CNRS">Institut de Chimie Organique et Analytique</idno>
            <idno type="stamp" n="INC-CNRS">Institut de Chimie du CNRS</idno>
            <idno type="stamp" n="CNRS_ICARE" corresp="UNIV-ORLEANS">Institut de Combustion Aérothermique Réactivité et Environnement</idno>
            <idno type="stamp" n="TEST-HALCNRS">Collection test HAL CNRS</idno>
            <idno type="stamp" n="ANR">ANR</idno>
            <idno type="stamp" n="TEST2-HALCNRS">TEST2-HALCNRS</idno>
            <idno type="stamp" n="LABOS-SYNORG">Labex SYNORG</idno>
            <idno type="stamp" n="PUBLIS-SYNORG">Publications financées par le Labex SYNORG</idno>
            <idno type="stamp" n="UNIVERSITE-BORDEAUX">Université de Bordeaux</idno>
          </seriesStmt>
          <notesStmt>
            <note type="audience" n="2">International</note>
            <note type="popular" n="0">No</note>
            <note type="peer" n="1">Yes</note>
          </notesStmt>
          <sourceDesc>
            <biblStruct>
              <analytic>
                <title xml:lang="en">Aminations and arylations by direct C–O activation for the design of 7,8-dihydro-6H -5,8-ethanopyrido[3,2- d]pyrimidines</title>
                <author role="aut">
                  <persName>
                    <forename type="first">Mazarine</forename>
                    <surname>Laurent</surname>
                  </persName>
                  <idno type="halauthorid">2240494-0</idno>
                  <affiliation ref="#struct-199928"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Stéphane</forename>
                    <surname>Bostyn</surname>
                  </persName>
                  <idno type="idhal" notation="numeric">773070</idno>
                  <idno type="halauthorid" notation="string">884016-773070</idno>
                  <idno type="ORCID">https://orcid.org/0000-0002-0313-9150</idno>
                  <affiliation ref="#struct-474628"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Mathieu</forename>
                    <surname>Marchivie</surname>
                  </persName>
                  <email type="md5">bbd5e0d094d38acb84d5ee7b5cbc2c00</email>
                  <email type="domain">icmcb.cnrs.fr</email>
                  <idno type="idhal" notation="string">mathieu-marchivie</idno>
                  <idno type="idhal" notation="numeric">735720</idno>
                  <idno type="halauthorid" notation="string">41834-735720</idno>
                  <idno type="IDREF">https://www.idref.fr/077034007</idno>
                  <idno type="ORCID">https://orcid.org/0000-0003-1362-0797</idno>
                  <idno type="VIAF">https://viaf.org/viaf/199905850</idno>
                  <idno type="ISNI">http://isni.org/isni/0000000357713960</idno>
                  <affiliation ref="#struct-525101"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Yves</forename>
                    <surname>Robin</surname>
                  </persName>
                  <idno type="halauthorid">145334-0</idno>
                  <affiliation ref="#struct-1072592"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Sylvain</forename>
                    <surname>Routier</surname>
                  </persName>
                  <email type="md5">02224a195402ffd13bdaec52362e2046</email>
                  <email type="domain">univ-orleans.fr</email>
                  <idno type="idhal" notation="string">sylvain-routier</idno>
                  <idno type="idhal" notation="numeric">936554</idno>
                  <idno type="halauthorid" notation="string">225531-936554</idno>
                  <idno type="IDREF">https://www.idref.fr/118636367</idno>
                  <idno type="ISNI">http://isni.org/isni/0000000430819818</idno>
                  <idno type="VIAF">https://viaf.org/viaf/173427768</idno>
                  <idno type="ORCID">https://orcid.org/0000-0002-2823-0591</idno>
                  <affiliation ref="#struct-199928"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Frédéric</forename>
                    <surname>Buron</surname>
                  </persName>
                  <email type="md5">9351b841c7c765a0f707d1039576fb6a</email>
                  <email type="domain">univ-orleans.fr</email>
                  <idno type="idhal" notation="string">frederic-buron</idno>
                  <idno type="idhal" notation="numeric">1103789</idno>
                  <idno type="halauthorid" notation="string">499611-1103789</idno>
                  <idno type="ORCID">https://orcid.org/0000-0001-5773-1515</idno>
                  <idno type="GOOGLE SCHOLAR">https://scholar.google.fr/citations?user=Q_4mAo4AAAAJ</idno>
                  <affiliation ref="#struct-199928"/>
                </author>
              </analytic>
              <monogr>
                <idno type="localRef">2021-092 (ICMCB)</idno>
                <idno type="halJournalId" status="VALID">101697</idno>
                <idno type="issn">2046-2069</idno>
                <title level="j">RSC Advances</title>
                <imprint>
                  <publisher>Royal Society of Chemistry</publisher>
                  <biblScope unit="volume">11</biblScope>
                  <biblScope unit="issue">32</biblScope>
                  <biblScope unit="pp">19363-19377</biblScope>
                  <date type="datePub">2021-05-28</date>
                </imprint>
              </monogr>
              <idno type="doi">10.1039/D1RA03092B</idno>
            </biblStruct>
          </sourceDesc>
          <profileDesc>
            <langUsage>
              <language ident="en">English</language>
            </langUsage>
            <textClass>
              <keywords scheme="author">
                <term xml:lang="en">Heterocyclic chemistry</term>
                <term xml:lang="en">Medicinal chemistry</term>
                <term xml:lang="en">Pyridine</term>
                <term xml:lang="en">Pyrimidine</term>
              </keywords>
              <classCode scheme="halDomain" n="chim.orga">Chemical Sciences/Organic chemistry</classCode>
              <classCode scheme="halDomain" n="chim.cata">Chemical Sciences/Catalysis</classCode>
              <classCode scheme="halDomain" n="chim.ther">Chemical Sciences/Medicinal Chemistry</classCode>
              <classCode scheme="halTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halOldTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halTreeTypology" n="ART">Journal articles</classCode>
            </textClass>
            <abstract xml:lang="en">
              <p>The design of some novel disubstituted 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidine derivatives is reported. The series was developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position C-2 that were then used to create C–N or C–C bonds for SNAr or palladium-catalyzed cross-coupling reactions by in situ C–O activation. The reaction conditions were optimized under microwave irradiation, and a wide range of amines or boronic acids were used to determine the scope and limitations of each method. To complete this study, the X-ray crystallographic data of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidine derivative 49 were used to formally establish the structures of the products.</p>
            </abstract>
          </profileDesc>
        </biblFull>
      </listBibl>
    </body>
    <back>
      <listOrg type="structures">
        <org type="laboratory" xml:id="struct-199928" status="VALID">
          <idno type="IdRef">166587664</idno>
          <idno type="ISNI">0000000403848680</idno>
          <idno type="RNSR">201220206R</idno>
          <idno type="ROR">https://ror.org/03ywn7d79</idno>
          <orgName>Institut de Chimie Organique et Analytique</orgName>
          <orgName type="acronym">ICOA</orgName>
          <date type="start">2012-01-01</date>
          <desc>
            <address>
              <addrLine>UFR Sciences Rue de Chartres - BP 6759 45067 ORLEANS CEDEX 2</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.icoa.fr</ref>
          </desc>
          <listRelation>
            <relation name="UMR 7311" active="#struct-300016" type="direct"/>
            <relation name="UMR 7311" active="#struct-300297" type="direct"/>
            <relation name="UMR 7311" active="#struct-303623" type="direct"/>
            <relation active="#struct-341038" type="direct"/>
            <relation name="UMR7311" active="#struct-441569" type="direct"/>
          </listRelation>
        </org>
        <org type="laboratory" xml:id="struct-474628" status="VALID">
          <idno type="IdRef">130578657</idno>
          <idno type="ISNI">0000000092583805</idno>
          <idno type="RNSR">200817616T</idno>
          <idno type="ROR">https://ror.org/03txr3336</idno>
          <idno type="Wikidata">Q30261464</idno>
          <orgName>Institut de Combustion, Aérothermique, Réactivité et Environnement</orgName>
          <orgName type="acronym">ICARE</orgName>
          <date type="start">2007-01-01</date>
          <desc>
            <address>
              <addrLine>1C, avenue de la Recherche Scientifique, CS 50060, 45071 - Orléans Cedex 2</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">https://icare.cnrs.fr/</ref>
          </desc>
          <listRelation>
            <relation name="UPR 3021" active="#struct-300297" type="direct"/>
            <relation name="UPR3021" active="#struct-441569" type="direct"/>
            <relation name="UPR3021" active="#struct-474627" type="direct"/>
          </listRelation>
        </org>
        <org type="laboratory" xml:id="struct-525101" status="VALID">
          <idno type="IdRef">151110174</idno>
          <idno type="ISNI">0000000087225173</idno>
          <idno type="RNSR">199017451S</idno>
          <idno type="ROR">https://ror.org/01nw6qk38</idno>
          <orgName>Institut de Chimie de la Matière Condensée de Bordeaux</orgName>
          <orgName type="acronym">ICMCB</orgName>
          <date type="start">2018-01-01</date>
          <desc>
            <address>
              <addrLine>87 Avenue du Docteur Schweitzer, 33608 PESSAC cedex</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.icmcb-bordeaux.cnrs.fr/</ref>
          </desc>
          <listRelation>
            <relation active="#struct-259761" type="direct"/>
            <relation active="#struct-301962" type="direct"/>
            <relation active="#struct-341038" type="direct"/>
            <relation name="UMR5026" active="#struct-441569" type="direct"/>
          </listRelation>
        </org>
        <org type="institution" xml:id="struct-1072592" status="INCOMING">
          <orgName>ISOCHEM</orgName>
          <desc>
            <address>
              <addrLine>4 Rue Marc Sangnier, 45300 Pithiviers</addrLine>
              <country key="FR"/>
            </address>
          </desc>
        </org>
        <org type="institution" xml:id="struct-300016" status="VALID">
          <idno type="IdRef">026372061</idno>
          <idno type="ISNI">0000000122998025</idno>
          <idno type="ROR">https://ror.org/00jjx8s55</idno>
          <idno type="Wikidata">Q868550</idno>
          <orgName>Commissariat à l'énergie atomique et aux énergies alternatives</orgName>
          <orgName type="acronym">CEA</orgName>
          <desc>
            <address>
              <addrLine>Centre de SaclayCentre de GrenobleCentre de Cadaracheetc</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.cea.fr/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-300297" status="VALID">
          <idno type="IdRef">026402971</idno>
          <idno type="ISNI">0000 0001 2158 1666</idno>
          <idno type="ROR">https://ror.org/014zrew76</idno>
          <orgName>Université d'Orléans</orgName>
          <orgName type="acronym">UO</orgName>
          <desc>
            <address>
              <addrLine>Château de la Source - Avenue du Parc Floral - BP 6749 - 45067 Orléans cedex 2</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.univ-orleans.fr/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-303623" status="VALID">
          <idno type="IdRef">026388278</idno>
          <idno type="ROR">https://ror.org/02vjkv261</idno>
          <orgName>Institut National de la Santé et de la Recherche Médicale</orgName>
          <orgName type="acronym">INSERM</orgName>
          <desc>
            <address>
              <addrLine>101, rue de Tolbiac, 75013 Paris</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.inserm.fr</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-341038" status="VALID">
          <idno type="IdRef">232435103</idno>
          <idno type="ISNI">000000010626358X</idno>
          <idno type="ROR">https://ror.org/02cte4b68</idno>
          <orgName>Institut de Chimie - CNRS Chimie</orgName>
          <orgName type="acronym">INC-CNRS</orgName>
          <date type="start">2009-10-01</date>
          <desc>
            <address>
              <addrLine>CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE3 rue Michel-Ange75794 PARIS CEDEX 16 - France</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.cnrs.fr/inc</ref>
          </desc>
        </org>
        <org type="regroupinstitution" xml:id="struct-441569" status="VALID">
          <idno type="IdRef">02636817X</idno>
          <idno type="ISNI">0000000122597504</idno>
          <idno type="ROR">https://ror.org/02feahw73</idno>
          <orgName>Centre National de la Recherche Scientifique</orgName>
          <orgName type="acronym">CNRS</orgName>
          <date type="start">1939-10-19</date>
          <desc>
            <address>
              <country key="FR"/>
            </address>
            <ref type="url">https://www.cnrs.fr/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-474627" status="VALID">
          <idno type="IdRef">232435111</idno>
          <idno type="ISNI">0000000405066498</idno>
          <idno type="ROR">https://ror.org/00s19x989</idno>
          <orgName>Institut des Sciences de l'Ingénierie et des Systèmes - CNRS Ingénierie</orgName>
          <orgName type="acronym">INSIS - CNRS</orgName>
          <date type="start">2009-11-01</date>
          <desc>
            <address>
              <addrLine>3 rue Michel-Ange, 75794, Paris cedex 16, France</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">https://www.insis.cnrs.fr/fr</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-259761" status="VALID">
          <idno type="IdRef">175206562</idno>
          <idno type="ROR">https://ror.org/057qpr032</idno>
          <orgName>Université de Bordeaux</orgName>
          <orgName type="acronym">UB</orgName>
          <desc>
            <address>
              <addrLine>35, place Pey Berland - 33076 Bordeaux</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.u-bordeaux.fr/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-301962" status="VALID">
          <idno type="ROR">https://ror.org/054qv7y42</idno>
          <orgName>Institut Polytechnique de Bordeaux</orgName>
          <desc>
            <address>
              <addrLine>146, rue Léo Saignat, 33076 Bordeaux</addrLine>
              <country key="FR"/>
            </address>
          </desc>
        </org>
      </listOrg>
      <listOrg type="projects">
        <org type="anrProject" xml:id="projanr-25520" status="VALID">
          <idno type="anr">ANR-11-LABX-0029</idno>
          <orgName>SYNORG</orgName>
          <desc>Synthèse Organique : des molécules au vivant</desc>
          <date type="start">2011</date>
        </org>
        <org type="anrProject" xml:id="projanr-26984" status="VALID">
          <idno type="anr">ANR-11-LABX-0018</idno>
          <orgName>IRON</orgName>
          <desc>Radiopharmaceutiques Innovants en Oncologie et Neurologie</desc>
          <date type="start">2011</date>
        </org>
      </listOrg>
    </back>
  </text>
</TEI>