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Diastereoselective synthesis of tetrahydropyrrolo[1,2-]oxadiazoles from functionalized Δ-pyrrolines and generated nitrile oxides. | LitMetric

AI Article Synopsis

  • - Tetrahydropyrrolo[1,2-]oxadiazoles were synthesized effectively through a cycloaddition reaction using nitrile oxides derived from aldoximes and functionalized Δ-pyrrolines.
  • - The reaction occurs at room temperature, utilizing sodium hypochlorite as an oxidant within a two-phase system, resulting in selective formation of important 1,2,4-oxadiazolines.
  • - This method is versatile and can handle various substrates, including those with sensitive functional groups and multiple reaction sites, making it promising for pharmaceutical applications.

Article Abstract

Tetrahydropyrrolo[1,2-]oxadiazoles have been synthesized in good-to-excellent yields the cycloaddition of nitrile oxides ( generated from aldoximes) to readily accessible functionalized Δ-pyrrolines. The reaction proceeds smoothly at room temperature in a two-phase system in the presence of sodium hypochloride as an oxidant to diastereoselectively afford pharmaceutically prospective 1,2,4-oxadiazolines fused with a five-membered ring. The reaction tolerates a broad range of substrates, including those with oxidant-sensitive functional groups and competitive reaction sites.

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Source
http://dx.doi.org/10.1039/d2ob02230cDOI Listing

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