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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{
  "@context": "https://schema.org/", 
  "@id": 53939, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA", 
      "name": "Young, Jonathon"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA", 
      "name": "Schafer, Christian"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA", 
      "name": "Solan, Agnes"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA", 
      "name": "Baldrica, Anthony"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA", 
      "name": "Belcher, Miranda"
    }, 
    {
      "@type": "Person", 
      "name": "Nisanci, Bilal"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Eastern Illinois Univ, Dept Chem, 600 Lincoln Ave, Charleston, IL 61920 USA", 
      "name": "Wheeler, Kraig A."
    }, 
    {
      "@type": "Person", 
      "affiliation": "Oakland Univ, Dept Chem, 146 Lib Dr, Rochester, MI 48309 USA", 
      "name": "Trivedi, Evan R."
    }, 
    {
      "@type": "Person", 
      "affiliation": "Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA", 
      "name": "Torok, Bela"
    }, 
    {
      "@type": "Person", 
      "name": "Dembinski, Roman"
    }
  ], 
  "datePublished": "2016-01-01", 
  "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.", 
  "headline": "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", 
  "identifier": 53939, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "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", 
  "url": "https://aperta.ulakbim.gov.tr/record/53939"
}