Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile: Selective Construction of l,4-Benzothiazine and Indole Ring Systems
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- HORIGUCHI Yoshie
- Showa Pharmaceutical University
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- SONOBE Akihiro
- Showa Pharmaceutical University
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- SAITOH Toshiaki
- Showa Pharmaceutical University
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- TODA Jun
- Showa Pharmaceutical University
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- SANO Takehiro
- Showa Pharmaceutical University
書誌事項
- タイトル別名
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- Intramolecular Capture of Pummerer Reaction Intermediates by an Aromatic Nucleophile: Selective Construction of 1,4-Benzothiazine and Indole Ring Systems.
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説明
The simple alkyl sulfoxide 6 carrying two aromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction conditions), underwent an intramolecular aromatic sulfenylation of the 6-exo-tet process in an exclusive manner to yield two regioisomeric 1, 4-benzothiazine derivatives, 8 and 9. On the other hand, a similar reaction of the α-acyl sulfoxide 7, possessing identical aromatic nucleophiles, caused an intramolecular aromatic alkylation of the 5-exo-trig process to produce the 3-oxo-indole derivative 14 in a quantitative yield. These results demonstrate that the construction of 1, 4-benzothiazine and indole ring systems can be achieved in a selective manner by proper choice of the sulfoxide side chain.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 49 (9), 1132-1137, 2001
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
- 1390001204164515328
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- NII論文ID
- 110003616062
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD3MXmsFyktrw%3D
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 5892758
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- PubMed
- 11558599
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- JaLC
- NDLサーチ
- Crossref
- PubMed
- CiNii Articles
- OpenAIRE
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- 抄録ライセンスフラグ
- 使用不可