Synthesis of <i>N</i>‐Alkyl and <i>N‐H</i>‐Carbazoles through S<sub>N</sub>Ar‐Based Aminations of Dibenzothiophene Dioxides

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  • Atsushi Kaga
    Department of Chemistry Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan
  • Keisuke Nogi
    Department of Chemistry Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan
  • Hideki Yorimitsu
    Department of Chemistry Graduate School of Science Kyoto University Sakyo-ku Kyoto 606-8502 Japan

書誌事項

公開日
2019-10-23
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/chem.201903916
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Alkyl amines have become available for the synthesis of diverse <jats:italic>N</jats:italic>‐alkyl carbazoles through twofold S<jats:sub>N</jats:sub>Ar aminations of dibenzothiophene dioxides by using alkali metal bases. Of particular importance is the choice of counter cations on alkali metal bases, that is, i) the use of Li base for the efficient intermolecular reaction and ii) the sequential addition of heavier alkali metal bases (Na, K, or Cs) to promote intramolecular cyclization in a one‐pot manner. This protocol also enables the cascade synthesis of <jats:italic>N‐H</jats:italic>‐carbazoles by using 2‐phenylethylamine by removal of the 2‐phenethyl group from <jats:italic>N‐</jats:italic>(2‐phenethyl) carbazoles in a single operation.</jats:p>

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