Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• acceptable to high yields. Mild reaction conditions, no requirement of metal catalysts, operational simplicity and the potential for scale-up production are some of the highlighted advantages of this transformation. Keywords: aniline; (E)-2-arylidene-3-cyclohexenone; imine condensation; isoaromatization

• was placed (E)-2-arylidene-3-cyclohexenone 2 (0.2 mmol), primary aliphatic amine 3 (2.0 mmol) and DME (2 mL). The reaction mixture was stirred at 60 °C and the reaction process was monitored by TLC analysis. After completion, the solvent was concentrated under reduced pressure and the residue was