A Deoxygenative [4+1] Annulation Involving N-Acyldiazenes for an Efficient Synthesis of 2,2,5-Trisubstituted 1,3,4-Oxadiazole Derivatives,Advanced Synthesis & Catalysis

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A Deoxygenative [4+1] Annulation Involving N-Acyldiazenes for an Efficient Synthesis of 2,2,5-Trisubstituted 1,3,4-Oxadiazole Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-14 12:51:37 , DOI: 10.1002/adsc.201700935
Rong Zhou ₁ , Ling Han ₁ , Honghui Zhang ₁ , Rongfang Liu ₁ , Ruifeng Li ₁

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An unprecedented and highly efficient tris(dimethylamino)phosphine [P(NMe₂)₃]-mediated deoxygenative [4 + 1] annulation of N-acyldiazenes with α-dicarbonyl compounds such as isatins, α-keto esters, and α-diketones is reported. The annulation reactions proceed smoothly under mild conditions to deliver a broad range of 2,2,5-trisubstituted 1,3,4-oxadiazole derivatives in moderate to excellent yields from readily available starting materials. It represents the first realization of the [4+1] annulation mode involving N-acyldiazenes to construct five-membered heterocycles.

中文翻译：

涉及N-酰基二氮烯的高效合成2,2,5-三取代的1,3,4-Oxadiazole衍生物的脱氧[4 + 1]环。

前所未有的，高效的三（二甲基氨基）膦[P（NMe ₂）₃ ]介导的N-酰基二氮烯与α-二羰基化合物（如靛红，α-酮酸酯和α-二酮）的脱氧[4 +1]环化反应报告。在温和的条件下，环化反应可顺利进行，从容易获得的起始原料中以中等至极好的收率提供各种2,2,5-三取代的1,3,4-恶二唑衍生物。它代表了[4 + 1]环化模式的第一个实现，该模式涉及N-酰基二氮烯以构建五元杂环。

更新日期：2017-11-15

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