Synthesis of 8-Methyltetrahydroquinoline derivatives functionalized at C-2: a one-pot tandem approach

Abstract

A new synthetic method, which achieves regiospecific functionalization of 8-methylquinoline derivatives at C-2 and subsequent selective hydrogenation of the pyridine ring in a one-pot tandem process, has been reported. With this method, a total of thirteen new 8-methyltetrahydroquinoline derivatives with an amide side chain at C-2 were synthesized in moderate yields. The scope of substrates was investigated, and the reaction mechanism was studied and proposed.

Graphical Abstract

Keywords:

• 8-methyltetrahydroquinoline derivatives
• nickel catalyst
• nucleophilic substitution
• hydrogenation
• one-pot synthesis

Additional information

Funding

The authors kindly acknowledge the financial support by the Robert A. Welch Foundation under Grant No. V-1815 and V-0004.