Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl)propionamides.
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The thionium ions 10 generated by Pummerer reaction of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides 4 caused not only an electrophilic cyclization reaction producing 2-quinolones 8, but also the formation of the vinyl sulfides 5 and 6 in favor of the latter reaction. On the other hand, the treatment of the vinyl sulfides 5 and 6 with p-toluenesulfonic acid induced cyclization to afford the 2-quinolones 8 in excellent to moderate yields, depending on the electronic properties of the aromatic ring, thus providing a convenient method for the snthesis of methoxy-2-quinolones.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 48 (12), 1854-1861, 2000
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
- 1390282679137908864
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- NII論文ID
- 130003947991
- 110003635388
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD3cXos1eisLc%3D
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- ISSN
- 13475223
- 00092363
- http://id.crossref.org/issn/00092363
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- NDL書誌ID
- 5582611
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- PubMed
- 11145131
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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
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可