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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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{
  "@context": "https://schema.org/", 
  "@id": 4525, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Karadeniz, Eda"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Kelgokmen, Yilmaz"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey", 
      "name": "Zora, Metin"
    }
  ], 
  "datePublished": "2021-01-01", 
  "description": "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.", 
  "headline": "A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones", 
  "identifier": 4525, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones", 
  "url": "https://aperta.ulakbim.gov.tr/record/4525"
}
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Karadeniz, E., Kelgokmen, Y. ve Zora, M. (2021). A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones. JOURNAL OF HETEROCYCLIC CHEMISTRY, 58(2), 466–477. doi:10.1002/jhet.4183

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