Model Experiments on Surugatoxin Synthesis. II. Synthesis of Ethyl 4-Amino-2-(6-bromo-2-oxo-3-indolinyl)-3-oxobutyrate Hydrochloride

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  • スルガトキシン合成に関するモデル実験(第2報)Ethyl 4-Amino-2-(6-bromo-2-oxo-3-indolinyl)-3-oxobutyrate Hydrochlorideの合成
  • スルガトキシン合成に関するモデル実験-2-Ethyl-4-Amino-2-(6-bromo-2-oxo-3-indolinyl)-3-oxobutyrate Hydrochlorideの合成
  • スルガトキシン ゴウセイ ニ カンスル モデル ジッケン 2 Ethyl 4

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Description

6-Bromoisatin, prepared from 2-nitroaniline in 7 steps, was condensed with ethyl 4-phthalimidoacetoacetate (10) under Knoevenagel conditions to give ethyl 2-(6-bromo-2-oxo-3-indolinylidene)-3-oxo-4-phthalimidobutyrate (11) in 83% yield. Reduction of 11 with sodium hydrosulfite in boiling EtOH afforded an enolized diastereomeric mixture of the oxindole derivative 12 (90%). Careful treatment of 12 with hydrazine hydrate followed by hydrolysis (10% HCl) gave amino-ketone hydrochloride 13 (49%).

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 105 (4), 357-361, 1985

    The Pharmaceutical Society of Japan

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