分子間interrupted Pummerer反応を利用したインドール類の官能基化反応

• 田湯 正法

  明治薬科大学

• 樋口 和宏

  明治薬科大学

• 川﨑 知己

  明治薬科大学

書誌事項

タイトル別名

• Functionalizations of Indoles by Intermolecular Interrupted Pummerer Reaction
• ブンシ カン interrupted Pummerer ハンノウ オ リヨウ シタ インドールルイ ノ カンノウキカ ハンノウ

抄録

A sulfonium species generated from sulfoxide and acid anhydride is a useful reagent for organic synthesis owing to its powerful electrophilicity. Among the various sulfonium-mediated reactions, interrupted Pummerer reaction has been well-investigated recently, which progresses the nucleophilic attack of substrate on sulfur atom of sulfonium such as Swern-type oxidation. Although interrupted Pummerer reactions are reported with various substrate such as alcohols, alkenes, enol ethers, the application to aromatics is limited because of the stability of initially generated arylthionium salts. In contrast, we previously developed intramolecular reaction via arylthionium intermediate for installing nucleophile to indole 2α-position in a one-pot procedure. This reaction was proceeded with special substrate by intramolecular reaction, therefore, it was unexplored as a general synthetic method. This article describes the details of the development of sulfonium species mediated reactions to functionalize indoles by intermolecular interrupted Pummerer reaction.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 76 (7), 678-689, 2018-07-01

  公益社団法人 有機合成化学協会

キーワード

• sulfonium
• interrupted Pummerer reaction
• indole

詳細情報

• CRID: 1390001288042673664
• NII論文ID: 130007403450
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.76.678
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 029156849
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029156849
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/76/7/76_678/_pdf
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可