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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  <dc:creator>Young, Jonathon</dc:creator>
  <dc:creator>Schafer, Christian</dc:creator>
  <dc:creator>Solan, Agnes</dc:creator>
  <dc:creator>Baldrica, Anthony</dc:creator>
  <dc:creator>Belcher, Miranda</dc:creator>
  <dc:creator>Nisanci, Bilal</dc:creator>
  <dc:creator>Wheeler, Kraig A.</dc:creator>
  <dc:creator>Trivedi, Evan R.</dc:creator>
  <dc:creator>Torok, Bela</dc:creator>
  <dc:creator>Dembinski, Roman</dc:creator>
  <dc:date>2016-01-01</dc:date>
  <dc:description>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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/53939</dc:identifier>
  <dc:identifier>oai:zenodo.org:53939</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>RSC ADVANCES 6(108) 107081-107093</dc:source>
  <dc: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</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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