Reaction of phthalic anhydrides with methyl isocyanoacetate: A useful synthesis of 1,2-dihydro-1-oxoisoquinolines.

• 沼波 憲一

• 鈴木 護

• 松本 和男

• 三好 宗次

• 米田 直人

抄録

Nitro-1, 2-dihydro-1-oxoisoquinoline-3-carboxylate compounds (5a, b and 9a, b) were synthesized by the reaction of methyl isocyanoacetate with nitrophthalic anhydrides in the presence of 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), followed by esterification with diazomethane and hydrolysis with HCl. In these reactions, the methylidenephthalide compound (10) was also obtained by hydrolysis of the oxazole-4-carboxylate compound (8b) due to the presence of the bulky ortho nitro group. Moreover, 1, 2-dihydro-4-hydroxy-1-oxoisoquinoline-3-carboxylic acid (16) was prepared via the oxazole dicarboxylic acid compound (15) in good yield.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 27 (6), 1373-1377, 1979

  公益社団法人 日本薬学会

キーワード

• ring transformation

詳細情報

• CRID: 1390001204173230080
• NII論文ID: 110003623665
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.27.1373
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/27/6/27_6_1373/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1980059893
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可