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One-Pot Synthesis of 2-Acety1-1H-pyrroles from N-Propargylic beta-Enaminones via Intermediacy of 1,4-Oxazepines

Kanova, Nilay; Dundar, Buse Aysen; Kelgokmen, Yilmaz; Zora, Metin


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{
  "DOI": "10.1021/acs.joc.1c00077", 
  "abstract": "A one pot two step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic beta-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic beta-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic beta-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.", 
  "author": [
    {
      "family": "Kanova", 
      "given": " Nilay"
    }, 
    {
      "family": "Dundar", 
      "given": " Buse Aysen"
    }, 
    {
      "family": "Kelgokmen", 
      "given": " Yilmaz"
    }, 
    {
      "family": "Zora", 
      "given": " Metin"
    }
  ], 
  "container_title": "JOURNAL OF ORGANIC CHEMISTRY", 
  "id": "231356", 
  "issue": "9", 
  "issued": {
    "date-parts": [
      [
        2021, 
        1, 
        1
      ]
    ]
  }, 
  "page": "6289-6304", 
  "title": "One-Pot Synthesis of 2-Acety1-1H-pyrroles from N-Propargylic beta-Enaminones via Intermediacy of 1,4-Oxazepines", 
  "type": "article-journal", 
  "volume": "86"
}
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