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Issue 36, 2020
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Iron-catalyzed radical cascade 6-endo cyclization of dienes towards fused nitrogen heterocycles initiated by an alkoxycarbonyl radical

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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.

Graphical abstract: Iron-catalyzed radical cascade 6-endo cyclization of dienes towards fused nitrogen heterocycles initiated by an alkoxycarbonyl radical

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Article information


Submitted
12 Jul 2020
Accepted
12 Aug 2020
First published
10 Sep 2020

Org. Biomol. Chem., 2020,18, 7086-7089
Article type
Communication

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

S. Qiao, P. Qian, F. Chen and J. Cheng, Org. Biomol. Chem., 2020, 18, 7086
DOI: 10.1039/D0OB01438A

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