Inyutina Anna, Dar'in Dmitry, Kantin Grigory, Krasavin Mikhail
Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
Org Biomol Chem. 2021 Jun 16;19(23):5068-5071. doi: 10.1039/d1ob00773d.
Attempted use of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in the Rh(ii)-catalyzed condensation with nitriles to form 1,3-oxazoles led to an unexpected outcome. The nitrilium ylide species thought to form on Rh(ii)-catalyzed decomposition of diazo compounds underwent a cyclization onto the nearby arylidene moiety followed by 1,5-hydride shift. This led to the formation of a 2-benzazepine core which has special significance for drug discovery and can be considered a privileged scaffold.
尝试使用（E）-3-亚芳基-4-重氮基吡咯烷-2,5-二酮在铑（II）催化下与腈缩合形成1,3-恶唑，结果出乎意料。据认为，在铑（II）催化下重氮化合物分解形成的腈叶立德物种在附近的亚芳基部分上发生环化，随后发生1,5-氢迁移。这导致形成了一个2-苯并氮杂卓核心，该核心在药物发现中具有特殊意义，可被视为一个特权骨架。
