The Chemistry of Indoles. XIII. Syntheses of Substituted Indoles carrying an Amino, Nitro, Methoxycarbonyl, or Benzyloxy Group at the 4-Position and Their 1-Hydroxy Derivatives

フォーマット:

論文

責任表示:

Somei, Masanori ; Inoue, Satomi ; Tokutake, Shoichi ; Yamada, Fumio ; Kaneko, Chikara

言語:

英語

出版情報:

Pharmaceutical Society of Japan = 日本薬学会, 1981-01-01

著者名:

• Somei, Masanori
• Inoue, Satomi
• Tokutake, Shoichi
• Yamada, Fumio
• Kaneko, Chikara

掲載情報:

Chemical and Pharmaceutical Bulletin

ISSN:

0009-2363      

巻:

29

通号:

3

開始ページ:

726

終了ページ:

738

バージョン:

publisher

概要:

Various 1-hydroxyindoles carrying a nitro, methoxycarbonyl, or benzyloxy group at the 4 position were prepared by the controlled reduction of 6-substituted trans-β-dimethylamino-2-nitrostyrenes with either aqueous titanium (III) chloride or zinc in aqueous ammonium chloride. The stability of 4-substituted 1-hydroxyindoles decreased in the following order : 4-nitro-»4-methoxycarbonyl->4-benzyloxy-1-hydroxyindole. This result … clearly indicates that an electron-withdrawing group at the 4-position can stabilize the 1-hydroxyindole structure. It was also found that 4-hydroxy-and 4-benzyloxy-indole were readily accessible by the reduction of 6-benzyloxy-2-nitrophenyl acetaldehyde. A unique route to 4-or 7-aminoindole from cinnoline is also described. 続きを見る

URL:

http://hdl.handle.net/2297/44024