title: Azocinoindole synthesis by a gold(I)-catalyzed ring expansion of 2-propargyl-β-tetrahydrocarboline.
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.
authors: State key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093 (P.R. China).
authors: Lei
authors: L
authors: Zhang
authors: Lina
authors: L
authors: Chang
authors: Hongwen
authors: H
authors: Hu
authors: Huaqin
authors: H
authors: Wang
authors: Zhu-Jun
authors: ZJ
authors: Yao
authors: Shaozhong
authors: S
authors: Wang
mesh_terms: D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C000597097:2-propargyl-beta-tetrahydrocarboline; D001392:Azocines; D002243:Carbolines; D007211:Indoles; C557359:azocino(4,3-b)indole; D006046:Gold
keywords: X-ray diffraction; gold; indoles; reaction mechanisms; ring expansion