Convenient Synthesis of Tetrahydro-γ-carbolines and Tetrahydroquinolines through a Chemo- and Regioselectivity Switch by a Brønsted Acid Catalyzed, One-Pot, Multicomponent Reaction

✍ Scribed by Hong-Gang Cheng; Cai-Bao Chen; Fen Tan; Ning-Jie Chang; Jia-Rong Chen; Wen-Jing Xiao

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 218 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000853

✦ Synopsis

Abstract

An efficient, one‐pot, multicomponent reaction of aldehydes 1, p‐methoxyaniline (2a), and 2‐vinylindoles 3 was developed. This approach provides a practical approach to synthetically and biologically significant tetrahydro‐γ‐carboline and tetrahydroquinoline derivatives in good yields through a chemo‐ and regioselectivity switch, which can be tuned by simply changing the substituent on the indole component under identical reaction conditions.