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A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones

Karadeniz, Eda; Kelgokmen, Yilmaz; Zora, Metin


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{
  "DOI": "10.1002/jhet.4183", 
  "abstract": "An efficient and general method for the synthesis of spiro-1,4-oxazepines and 3,3-dimethyl-1,4-oxazepines is reported. When treated with ZnI2 and AgSbF6 in refluxing DCE, cyclohexane-embedded N-propargylic beta-enaminones underwent 7-exo-dig cyclization to afford spiro-1,4-oxazepines, specifically 12-methylene-11-oxa-7-azaspiro[5.6]dodeca-7,9-dienes, in good to high yields. Accordingly, N-(1,1-dimethyl)propargylic beta-enaminones produced 3,3-dimethyl-1,4-oxazepines. Cyclization was found to be general for a diverse range of N-propargylic beta-enaminones with high efficiency and broad functional group tolerance. This operationally easy method might provide quick access to a library of functionalized spiro and gem-dimethyl-substituted 1,4-oxazepine derivatives of pharmacological interest.", 
  "author": [
    {
      "family": "Karadeniz", 
      "given": " Eda"
    }, 
    {
      "family": "Kelgokmen", 
      "given": " Yilmaz"
    }, 
    {
      "family": "Zora", 
      "given": " Metin"
    }
  ], 
  "container_title": "JOURNAL OF HETEROCYCLIC CHEMISTRY", 
  "id": "4525", 
  "issue": "2", 
  "issued": {
    "date-parts": [
      [
        2021, 
        1, 
        1
      ]
    ]
  }, 
  "page": "466-477", 
  "title": "A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones", 
  "type": "article-journal", 
  "volume": "58"
}
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