A new indole synthesis via rearrangements of N-propargylaniline N-oxides. A one-pot synthesis of indole-3-acetonitriles.
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A new, general method was developed for the synthesis of 3-(substituted-methyl)-indoles from N-propargylanilines. The method involves oxidation of the aniline with m-chloroperbenzoic acid and subsequent treatment with a suitable nucleophilic reagent under mild conditions in a single flask. The possible pathway was indicated to be (a) formation of an N-oxide, (b) [2, 3] and [3, 3] sigmatropic rearrangements of a propargyl group, (c) formation of a 3-methylideneindolenine intermediate, and (d) an attack of a nucleophilic reagent on the methylidene function. The process was quite general and provided a new route for synthesizing 3-(substituted-methyl) indoles-for example, indole-3-acetonitriles, 3-phenylthiomethylindoles, 3-azidomethylindoles and their derivatives.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 24 (4), 770-777, 1976
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
- 1390001204172700544
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- NII論文ID
- 110003635042
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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
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可