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铁催化的二烯自由基级联 6-环化反应,通过烷氧基羰基自由基引发稠合氮杂环。

Iron-catalyzed radical cascade 6- cyclization of dienes towards fused nitrogen heterocycles initiated by an alkoxycarbonyl radical.

机构信息

School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou 213164, P. R. China.

Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China.

出版信息

Org Biomol Chem. 2020 Sep 23;18(36):7086-7089. doi: 10.1039/d0ob01438a.

Abstract

An iron-catalyzed radical cascade cyclization of dienes initiated by an alkoxycarbonyl radical has been developed in the presence of (NH4)2S2O8, leading to a series of fused nitrogen heterocyclic compounds under relatively mild reaction conditions. The reaction is triggered by the addition of an alkyoxycarbonyl radical derived from the cleavage of alkoxyformyl hydrazide. Afterward, the formed nucleophilic radical preferred addition to the electron-neutral vinyl rather than the electron-deficient vinyl, followed by cascade 6-endo cyclization and further radical cyclization.

摘要

在过硫酸铵((NH4)2S2O8)的存在下,开发了一种由烷氧基羰基自由基引发的二烯的铁催化自由基级联环化反应,在相对温和的反应条件下得到一系列稠合氮杂环化合物。反应由烷氧基甲酰基酰肼裂解生成的烷氧基羰基自由基引发。随后,形成的亲核自由基优先与电中性的乙烯基而不是缺电子的乙烯基加成,然后进行级联 6-endo 环化和进一步的自由基环化。

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