One‐potCuAAC synthesis of (1H‐1,2,3‐triazol‐1‐yl)methyl‐1,3,4/1,2,4‐oxadiazoles starting from available chloromethyl‐1,3,4/1,2,4‐oxadiazoles,Journal of Heterocyclic Chemistry

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One‐potCuAAC synthesis of (1H‐1,2,3‐triazol‐1‐yl)methyl‐1,3,4/1,2,4‐oxadiazoles starting from available chloromethyl‐1,3,4/1,2,4‐oxadiazoles
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-05-05 , DOI: 10.1002/jhet.4008
Nazariy T. Pokhodylo ₁ , Roman D. Savka ₁ , Olga Ya. Shyyka ₁ , Mykola D. Obushak ₁

Affiliation

The one‐pot CuAAC synthesis of (1H ‐1,2,3‐triazol‐1‐yl)methyl‐1,3,4‐oxadiazole and (1H ‐1,2,3‐triazol‐1‐yl)methyl‐1,2,4‐oxadiazole derivatives via three‐component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “click” reaction, with alkynes, in the presence of CuI was studied. The utility of newly synthesized 2‐(azidomethyl)‐1,3,4/1,2,4‐oxadiazoles and chloromethyl‐1,3,4/1,2,4‐oxadiazole derivatives was explored, and their limitations were determined. Novel 5‐([4‐aryl‐1H ‐1,2,3‐triazol‐1‐yl]methyl)‐3‐(aryl)‐1,2,4‐oxadiazoles, 2‐([4‐aryl‐1H ‐1,2,3‐triazol‐1‐yl]methyl)‐5‐(aryl)‐1,3,4‐oxadiazoles were obtained in good yields.

中文翻译：

从可用的氯甲基-1,3,4 / 1,2开始，一锅CuAAC合成（1H-1,2,3-三唑-1-基）甲基-1,3,4 / 1,2,4-恶二唑， 4-恶二唑

一锅法CuAAC合成（1 H -1,2,3-三唑-1基）甲基-1,3,4-恶二唑和（1 H -1,2,3-三唑-1基）甲基研究了通过与叠氮化物的随后亲核取代氯反应的三组分反应制得的1,2,4-恶二唑衍生物，以及在CuI存在下与炔烃进行的进一步“点击”反应。探索了新合成的2-（叠氮甲基）-1,3,4 / 1,2,4-恶二唑和氯甲基-1,3,4 / 1,2,4-恶二唑衍生物的效用，并确定了它们的局限性。新型5-（[[4-芳基-1 H -1,2,3-三唑-1-基]甲基] -3-（芳基）-1,2,4-恶二唑，2-（[4-芳基-1以高收率获得了H -1,2,3-三唑-1-甲基] -5-（芳基）-1,3,4-恶二唑。

更新日期：2020-05-05

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