インドール-2,3-エポキシド代替品の開発と応用

DOI Web Site Web Site 被引用文献2件 参考文献65件

書誌事項

タイトル別名
  • Development and Application of Indole-2,3-epoxide Surrogates
  • インドール-2,3-エポキシド ダイタイヒン ノ カイハツ ト オウヨウ

この論文をさがす

抄録

<p>C3-Nucleophilic substitution of indoles has been limited because the transformation requires an umpolung of the C3 position of indoles. Among the indole derivatives, indole-2,3-epoxides could be potentially be used as C3-electrophilic reagents due to the electrophilic nature of the C2 and C3 positions. However, their use as C3 electrophilic reagents has not been possible so far due to their instability.</p><p>We describe a novel and bench stable surrogate of indole-2,3-epoxide, 2-hydroxyindoline-3-triethylammonium bromide (HITAB), which was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with nucleophiles. By taking advantage of the nucleophilic character of the oxygen of the 2-hydroxyindoline, interrupted retro-Claisen and interrupted Feist-Bénary reactions with 1,3-dicarbonyl compounds, one-pot formation of furodiindolines from 3-substituted indoles were achieved. Furthermore, we developed a novel cascade reaction of the indole-2,3-epoxide surrogate with γ-carbolines to access multiheterocyclic compounds containing both isotryptamines and pyrimido［1,6-a］indoles. This reaction utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences. The synthetic potential of the ammonium salts was demonstrated by the short synthesis of cryptolepine, iheyamine A, racemocine B derivative, and neocryptolepine derivative.</p>

収録刊行物

被引用文献 (2)*注記

もっと見る

参考文献 (65)*注記

もっと見る

キーワード

詳細情報 詳細情報について

問題の指摘

ページトップへ