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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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        "affiliation": "Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey", 
        "name": "Ismailoglu, Eda"
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      {
        "affiliation": "Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey", 
        "name": "Mert, Zeynep"
      }, 
      {
        "affiliation": "Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey", 
        "name": "Dinc, Mert"
      }, 
      {
        "affiliation": "Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey", 
        "name": "Kaya, Kerem"
      }, 
      {
        "affiliation": "Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey", 
        "name": "Yucel, Baris"
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    "description": "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.", 
    "doi": "10.1002/ejoc.202100483", 
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      "issue": "29", 
      "pages": "4107-4124", 
      "title": "EUROPEAN JOURNAL OF ORGANIC CHEMISTRY", 
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    "title": "Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines"
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