| 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 |
Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles |
| 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 |
Nishiwaki, Nagatoshi
Kobiro, Kazuya
Hirao, Shotaro
Sawayama, Jun
Saigo, Kazuhiko
Ise, Yumiko
Okajima, Yoshikazu
Ariga, Masahiro
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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 |
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 |
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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 |
10.1039/C1OB05682D |
| 権利（URI） |
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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 |
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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 |
Royal Society of Chemistry |
27-18.pdf (215.3 kB)
