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Design and Synthesis of Pyrrolotriazepine Derivatives: An Experimental and Computational Study

Menges, Nurettin; Sari, Ozlem; Abdullayev, Yusif; Erdem, Safiye Sag; Balci, Metin


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/16625</identifier>
  <creators>
    <creator>
      <creatorName>Menges, Nurettin</creatorName>
      <givenName>Nurettin</givenName>
      <familyName>Menges</familyName>
    </creator>
    <creator>
      <creatorName>Sari, Ozlem</creatorName>
      <givenName>Ozlem</givenName>
      <familyName>Sari</familyName>
    </creator>
    <creator>
      <creatorName>Abdullayev, Yusif</creatorName>
      <givenName>Yusif</givenName>
      <familyName>Abdullayev</familyName>
    </creator>
    <creator>
      <creatorName>Erdem, Safiye Sag</creatorName>
      <givenName>Safiye Sag</givenName>
      <familyName>Erdem</familyName>
      <affiliation>Marmara Univ, Dept Chem, TR-34722 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Balci, Metin</creatorName>
      <givenName>Metin</givenName>
      <familyName>Balci</familyName>
      <affiliation>Middle E Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Design And Synthesis Of Pyrrolotriazepine Derivatives: An Experimental And Computational Study</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2013</publicationYear>
  <dates>
    <date dateType="Issued">2013-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/16625</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/jo4001228</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 pyrrole derivatives having carbonyl groups at the C-2 position were converted to N-propargyl pyrroles. The reaction of those compounds with hydrazine monohydrate resulted in the formation of 5H-pyrrolo[2,1-d][1,2,5]-triazepine derivatives. The synthesis of these compounds was accomplished in three steps starting from pyrrole. On the other hand, attempted cyclization of a pyrrole ester substituted with a propargyl group at the nitrogen atom gave, unexpectedly, the six-membered cyclization product, 2-amino-3-methylpyrrolo[1,2-a]pyrazin-1(2H)-one as the major product. The expected cyclization product with a seven-membered ring, 4-methyl-2,3-dihydro-1H-pyrrolo[2,1-d][1,2,5]-triazepin-1-one was formed as the minor product and was converted quantitatively to the major product. The formation mechanism of the products was investigated, and the results obtained were also supported by theoretical calculations.</description>
  </descriptions>
</resource>
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