通过铁（III）盐介导的硅氮杂-Prins环化反应合成四氢氮杂卓
Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts.
作者信息
Sinka Victoria, Fernández Israel, Padrón Juan I
机构信息
Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, 38206, Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife (Spain).
Departamento de Química Orgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain.
出版信息
J Org Chem. 2022 Sep 2;87(17):11735-11742. doi: 10.1021/acs.joc.2c01396. Epub 2022 Aug 17.
A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C-N, C-C bond and an endocyclic double bond are formed. Under mild reaction conditions and using iron(III) salts as sustainable catalysts, tetrahydroazepines with different degrees of substitution are obtained directly and efficiently. DFT calculations supported the proposed mechanism.
开发了一种合成七元不饱和氮杂环（四氢氮杂卓）的新方法。它基于强大的氮杂-Prins环化反应与彼得森型消除反应相结合。在单个反应步骤中，形成了一个C-N、C-C键和一个内环双键。在温和的反应条件下，使用铁（III）盐作为可持续催化剂，可以直接且高效地获得不同取代度的四氢氮杂卓。密度泛函理论计算支持了所提出的机理。
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