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Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles
http://hdl.handle.net/10173/1370
http://hdl.handle.net/10173/13709c7dfb51-042b-4eae-866a-ebfca87172d8
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
27-18.pdf (215.3 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2016-03-25 | |||||
| タイトル | ||||||
| タイトル | Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
Nishiwaki, Nagatoshi
× Nishiwaki, Nagatoshi× Kobiro, Kazuya× Hirao, Shotaro× Sawayama, Jun× Saigo, Kazuhiko× Ise, Yumiko× Okajima, Yoshikazu× Ariga, Masahiro |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2,4-oxadiazoles, which are expected to serve as precursors for the preparation of a variety of functional materials by the chemical transformation of the carbamoyl group. While conventional preparative methods for 1,2,4-oxadiazoles involve the cycloaddition of an electron-rich nitrile oxide with an electron-deficient nitrile or a nitrile activated by a Lewis acid, our method employs the complementary combination of an electron-rich nitrile and an electron-deficient nitrile oxide- the inverse electron-demand 1,3-cycloaddition. The DFT calculations using B3LYP 6-31G* supported the abovementioned inverse reactivity, and also suggested the presence of an accelerating effect by the carbamoyl group as a result of hydrogen bond formation with a dipolarophilic nitrile. | |||||
| 書誌情報 |
Organic & Biomolecular Chemistry 巻 9, 号 19, p. 6750-6754, 発行日 2011 |
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| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1039/C1OB05682D | |||||
| 権利（URI） | ||||||
| 権利情報 | http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract | http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract | |||||
| 著者版フラグ | ||||||
| 出版タイプ | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
| 出版者 | ||||||
| 出版者 | Royal Society of Chemistry | |||||
