Studies on the syntheses of heterocyclic compounds. DCCLV. Iminoketene cycloaddition. 4. Alternative syntheses of 5,6,7,8-tetrahydro-2,3-dimethoxy-8-oxoisoquinolo[1,2-b]quinazoline and rutecarpine.
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Treatment of the sulfinamide anhydride (2), prepared from anthranilic acid (1), with 3, 4-dihydro-6, 7-dimethoxyisocarbostyril (9) gave 5, 6, 7, 8-tetrahydro-2, 3-dimethoxy-8-oxoisoquinolo [1, 2-b] quinazoline (10), which was also obtained by heating isatoic anhydride (3) with 9. Similarly, rutecarpine (6) was synthesised by the reactions of 1, 2, 3, 4-tetrahydro-1-keto-β-carboline (13) with the sulfinamide anhydride (2) or isatoic anhydride (3). Heating 3, 4-dihydro-β-carboline (5) with 3 also afforded rutecarpine (6). Furthermore the phosphates (8a) and (12) were isolated on treatment of the urethanes (7a) and (11) with phosphoryl chloride.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 26 (6), 1922-1926, 1978
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204171027584
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- NII論文ID
- 110003623224
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
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- CiNii Articles
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- 使用不可