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Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

Ismailoglu, Eda; Mert, Zeynep; Dinc, Mert; Kaya, Kerem; Yucel, Baris


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{
  "DOI": "10.1002/ejoc.202100483", 
  "abstract": "1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30-87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30-94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A(3)-coupling reaction.", 
  "author": [
    {
      "family": "Ismailoglu", 
      "given": " Eda"
    }, 
    {
      "family": "Mert", 
      "given": " Zeynep"
    }, 
    {
      "family": "Dinc", 
      "given": " Mert"
    }, 
    {
      "family": "Kaya", 
      "given": " Kerem"
    }, 
    {
      "family": "Yucel", 
      "given": " Baris"
    }
  ], 
  "container_title": "EUROPEAN JOURNAL OF ORGANIC CHEMISTRY", 
  "id": "234850", 
  "issue": "29", 
  "issued": {
    "date-parts": [
      [
        2021, 
        1, 
        1
      ]
    ]
  }, 
  "page": "4107-4124", 
  "title": "Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines", 
  "type": "article-journal", 
  "volume": "2021"
}
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