| Item type |
学術雑誌論文 / Journal Article(1) |
| 公開日 |
2016-03-25 |
| タイトル |
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タイトル |
Reactive 2-Quinolones Dearomatized by Steric Repulsion between 1-Methyl and 8-Substited Groups |
| 言語 |
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言語 |
eng |
| 資源タイプ |
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資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 著者 |
Chen, Xin
Kobiro, Kazuya
Asahara, Haruyasu
Kakiuchi, Kiyomi
Sugimoto, Ryuichi
Saigo, Kazuhiko
Nishiwaki, Nagatoshi
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| 抄録 |
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内容記述タイプ |
Abstract |
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内容記述 |
Usual 1-methyl-2-quinolone (MeQone) derivatives are not reactive because of aromatic property in the heterocyclic ring. On the other hand, 8-substituted MeQones have been proved to be highly reactive, which is caused by steric repulsion between the 1-methyl and the 8-substituted groups. When 1-methyl-3,6,8-trinitro-2-quinolone was treated with potassium (or trimethylsilyl) cyanide, cyanation proceeded at the 4-position regioselectively as a result of cine-substitution. This reaction is initiated with addition of cyanide species, and the cyanoquinolone is formed by the protonation of the resultant anionic intermediate followed by elimination of nitrous acid. The high reactivity was maintained even when one of the nitro groups on the benzene moiety was replaced by a methyl group, which afforded corresponding cine-substituted products upon treatment with potassium cyanide. |
| 書誌情報 |
Tetrahedron
巻 69,
号 23,
p. 4624-4630,
発行日 2013
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| DOI |
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関連タイプ |
isVersionOf |
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識別子タイプ |
DOI |
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関連識別子 |
10.1016/j.tet.2013.04.008 |
| 著者版フラグ |
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出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| 出版者 |
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出版者 |
Elsevier Ltd. |
27-22.pdf (323.8 kB)
