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N-酰基苯并三唑在合成 5-取代 2-乙氧基-1,3,4-噁二唑作为构建块用于 3,5-二取代 1,3,4-噁二唑-2(3H)-酮中的应用。

Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones.

机构信息

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, ‡Graduate School, and §Center of Excellence in Materials Science and Technology, Chiang Mai University , Chiang Mai 50200, Thailand.

出版信息

J Org Chem. 2017 Sep 15;82(18):9923-9929. doi: 10.1021/acs.joc.7b01863. Epub 2017 Sep 1.

Abstract

5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of PhP-I as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.

摘要

5-取代-2-乙氧基-1,3,4-噁二唑可以通过在苯膦-碘作为脱水剂的存在下,乙基碳酰胺和 N-酰基苯并三唑之间的一锅法顺序 N-酰化/脱水环化反应方便地制备。随后用等摩尔量的卤代烃(X=Cl、Br、I)处理,可以快速得到各种 3,5-二取代的 1,3,4-噁二唑-2(3H)-酮,产率良好至优秀。

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