A Synthesis of 1-Azaanthraquinones via Diels-Alder Reaction of 4-Hydroxy- and 4-Methoxy-2-phenylquinolinequinones with 3-Trimethylsilyloxy-1,3-butadienes: Observation of Inverse Regioselectivity.

• HORIGUCHI Yoshie

• TOEDA Akio

• TOMODA Katuhiro

• SUZUKI Hideki

• SANO Takehiro

書誌事項

タイトル別名

• Synthesis of 1-Azaanthraquinones via Di

抄録

Diels-Alder reaction of 4-hydroxy-2-phenylquinolinequinone (10a) and 4-methoxy-2-phenylquinoline-quinone (10b) with 1-methoxy-3-trimethylsilyloxybutadiene proceeded in a highly regio- and stereoselective manner to give the [4+2] adducts (11) and (14) in good yields, respectively. The structures of the adducts and their derivatives were unambiguously determined by spectroscopic data, including high resolution heteronuclear multi bond correlation. The quinolinequinones (10a and 10b) gave inverse regioselectivity. This is related to the presence of the hydroxy group or the methoxy group at the C-4 position. These results demonstrated that Diels-Alder reaction of azadienophiles with activated dienes provides a versatile method for synthesizing 4-oxygenated 1-azaanthraquinones.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 46 (9), 1356-1363, 1998

  公益社団法人 日本薬学会

キーワード

• Diels-Alder reaction
• quinolinequinone
• regioselectivity
• 1-methoxy-3-trimethylsilyloxybutadine
• 1-azaanthraquinone

詳細情報

• CRID: 1390282679137285376
• NII論文ID: 130003773849
• NII論文ID: 110003617039
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.46.1356
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 4573180
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4573180
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/46/9/46_9_1356/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可