Azocinoindole Synthesis by a Gold(I)‐Catalyzed Ring Expansion of 2‐Propargyl‐β‐Tetrahydrocarboline. Issue 10 (12th February 2014)

• Record Type: Journal Article
• Authors: Zhang, Lei; Chang, Lina; Hu, Hongwen; Wang, Huaqin; Yao, Zhu‐Jun; Wang, Shaozhong
• Is Part Of: Chemistry. Volume 20:Issue 10(2014)
• Page Start: 2925
• Page End: 2932
• Publication Date: 2014-02-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201304524
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new methodology taking advantage of gold(I)‐catalyzed ring expansion has been developed to assemble tricyclic 1<italic>H</italic>‐azocino[5, 4‐<italic>b</italic>]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.</p> </abstract>