Azocinoindole Synthesis by a Gold(I)‐Catalyzed Ring Expansion of 2‐Propargyl‐β‐Tetrahydrocarboline |
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| Authors: | Lei Zhang Lina Chang Prof. Hongwen Hu Huaqin Wang Prof. Dr. Zhu‐Jun Yao Prof. Dr. Shaozhong Wang |
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| Affiliation: | 1. State key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China);2. Modern Analytical Center of Nanjing University, Nanjing 210093 (P.R. China) |
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| Abstract: | A new methodology taking advantage of gold(I)‐catalyzed ring expansion has been developed to assemble tricyclic 1H‐azocino[5,4‐b]indoles from 2‐propargyl‐β‐tetrahydrocarbolines. The azocinoindoles were obtained in moderate to excellent yields; the structure of which was established by X‐ray crystallographic analysis. A mechanism involving regioselective intramolecular hydroarylation, [1,2]‐alkenyl migration and carbon–carbon bond‐fragmentation was proposed. |
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| Keywords: | gold indoles reaction mechanisms ring expansion X‐ray diffraction |
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