Construction of diverse polycyclic N-heterocycles via cascade allylic amination/Diels-Alder reaction
Zhenkun Yang1, Hongling Xie1, Luning Tang1
1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, China. huanghai@cczu.edu.cn.
Abstract:
An efficient cascade approach for the construction of nitrogen-containing polycyclic compounds from amines tethered with an alkenyl (or alkynyl) group and divinyl carbonates is described. In the presence of Pd(0)-catalyst, an active zwitterionic allylpalladium species is generated and undergoes allylic amination with various amines followed by Diels-Alder reaction to form various polycyclic N-heterocyclic products, including hydrophenanthridines, hydrobenzo[c]azepines (hydro)isoindoles and hydrobenzo[cd]indoles.
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The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...


