1613190-60-5Relevant articles and documents
Azocinoindole synthesis by a gold(I)-catalyzed ring expansion of 2-propargyl-β-tetrahydrocarboline
Zhang, Lei,Chang, Lina,Hu, Hongwen,Wang, Huaqin,Yao, Zhu-Jun,Wang, Shaozhong
, p. 2925 - 2932 (2014/03/21)
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. Route to ring expansion: 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 (see scheme; EWG= electron-withdrawing group). A mechanism involving regioselective hydroarylation, [1,2]-alkenyl migration, and carbon-carbon bond fragmentation was proposed.