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

Citation Style Language JSON

{
  "DOI": "10.1039/c6ra24291j", 
  "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.", 
  "author": [
    {
      "family": "Young", 
      "given": " Jonathon"
    }, 
    {
      "family": "Schafer", 
      "given": " Christian"
    }, 
    {
      "family": "Solan", 
      "given": " Agnes"
    }, 
    {
      "family": "Baldrica", 
      "given": " Anthony"
    }, 
    {
      "family": "Belcher", 
      "given": " Miranda"
    }, 
    {
      "family": "Nisanci", 
      "given": " Bilal"
    }, 
    {
      "family": "Wheeler", 
      "given": " Kraig A."
    }, 
    {
      "family": "Trivedi", 
      "given": " Evan R."
    }, 
    {
      "family": "Torok", 
      "given": " Bela"
    }, 
    {
      "family": "Dembinski", 
      "given": " Roman"
    }
  ], 
  "container_title": "RSC ADVANCES", 
  "id": "53939", 
  "issue": "108", 
  "issued": {
    "date-parts": [
      [
        2016, 
        1, 
        1
      ]
    ]
  }, 
  "page": "107081-107093", 
  "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", 
  "type": "article-journal", 
  "volume": "6"
}