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Azocinoindole Synthesis by a Gold(I)‐Catalyzed Ring Expansion of 2‐Propargyl‐β‐Tetrahydrocarboline
Author(s) -
Zhang Lei,
Chang Lina,
Hu Hongwen,
Wang Huaqin,
Yao ZhuJun,
Wang Shaozhong
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304524
Subject(s) - propargyl , intramolecular force , regioselectivity , ring (chemistry) , catalysis , chemistry , fragmentation (computing) , stereochemistry , organic chemistry , computer science , operating system
A new methodology taking advantage of gold(I)‐catalyzed ring expansion has been developed to assemble tricyclic 1 H ‐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.