1 Ocak 2016 Dergi makalesi Açık Erişim

Young, Jonathon; Schafer, Christian; Solan, Agnes; Baldrica, Anthony; Belcher, Miranda; Nisanci, Bilal; Wheeler, Kraig A.; Trivedi, Evan R.; Torok, Bela; Dembinski, Roman

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/53939</identifier>
  <creators>
    <creator>
      <creatorName>Young, Jonathon</creatorName>
      <givenName>Jonathon</givenName>
      <familyName>Young</familyName>
      <affiliation>Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Schafer, Christian</creatorName>
      <givenName>Christian</givenName>
      <familyName>Schafer</familyName>
      <affiliation>Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Solan, Agnes</creatorName>
      <givenName>Agnes</givenName>
      <familyName>Solan</familyName>
      <affiliation>Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Baldrica, Anthony</creatorName>
      <givenName>Anthony</givenName>
      <familyName>Baldrica</familyName>
      <affiliation>Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Belcher, Miranda</creatorName>
      <givenName>Miranda</givenName>
      <familyName>Belcher</familyName>
      <affiliation>Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Nisanci, Bilal</creatorName>
      <givenName>Bilal</givenName>
      <familyName>Nisanci</familyName>
    </creator>
    <creator>
      <creatorName>Wheeler, Kraig A.</creatorName>
      <givenName>Kraig A.</givenName>
      <familyName>Wheeler</familyName>
      <affiliation>Eastern Illinois Univ, Dept Chem, 600 Lincoln Ave, Charleston, IL 61920 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Trivedi, Evan R.</creatorName>
      <givenName>Evan R.</givenName>
      <familyName>Trivedi</familyName>
      <affiliation>Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Torok, Bela</creatorName>
      <givenName>Bela</givenName>
      <familyName>Torok</familyName>
      <affiliation>Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Dembinski, Roman</creatorName>
      <givenName>Roman</givenName>
      <familyName>Dembinski</familyName>
    </creator>
  </creators>
  <titles>
    <title>Regioselective "Hydroamination" Of Alk-3-Ynones With Non-Symmetrical O-Phenylenediamines. Synthesis Of Diversely Substituted 3H-1,5-Benzodiazepines Via (Z)-3-Amino-2-Alkenones</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2016</publicationYear>
  <dates>
    <date dateType="Issued">2016-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/53939</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1039/c6ra24291j</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">The reaction of alk-3-yn-1-ones (a bifunctional reagent) with o-phenylenediamines provides an effective synthetic method with high atom economy for the preparation of diversely substituted 1,5-3H-benzodiazepines. The reaction initially leads to the formation of conjugated enaminones (3-amino-2alkenones, 51-99%), at room temperature, which constitutes a formal non-catalyzed hydroamination of the non-conjugated alkyne. Non-symmetrical o-phenylenediamines react in a regioselective fashion with respect to amino groups. Both the direct microwave-accelerated reaction of o-phenylenediamines with alkynones in ethanol and the intramolecular cyclization of intermediate enaminones in ethanol/acetic acid lead to substituted 1,5-benzodiazepines with good yields (39-92 and 26-99%). The regio-and stereochemical outcomes of these processes are confirmed by the X-ray structure determination of (Z)-3-[(2-amino-4-methylanilino)-4-(4-methylphenyl)-1-phenylbut-2-en-1-one],4-[(4-methylphenyl) methyl]-7-nitro-2-phenyl-3H-1,5-benzodiazepine and 6,8-dimethyl-4-(4-methylbenzyl)-2-phenyl-3Hbenzo[b][1,5]diazepine.</description>
  </descriptions>
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