Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans,Synthesis

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Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans
Synthesis ( IF 2.2 ) Pub Date : 2020-05-05 , DOI: 10.1055/s-0040-1707393
Leonid L. Fershtat ₁ , Daniil A. Chaplygin ₁ , Ivan V. Ananyev _{2,

3} , Nina N. Makhova ₁

Affiliation

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.

中文翻译：

通过4-芳基呋喃烷的级联反应发散合成五元氮杂环

开发了一种通过原子-经济，区域和非对映选择性一锅反应级联反应合成一系列功能取代的五元杂环化合物的新方法。该方法涉及在4-芳基呋喃烷中向α-氧亚氨基芳基乙腈氧化物开环，然后将[3 + 2]环加成至各种偶极亲和剂中，以提供多取代的异恶唑和异恶唑啉。随后可以单锅法进行的（肟基）异恶唑啉/异恶唑的唑-唑重排导致功能性取代的呋喃酮的形成。所开发的方案操作简单，在温和条件下进行，目标杂环系统收率高。总体而言，这项研究代表了异恶唑和1,2,5-恶二唑功能化策略的新模式，

更新日期：2020-05-05

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