Efficient InCl₃/H₂O-Catalyzed One-Pot Stereoselective Synthesis of cis-2-Methyl-4-amido-1,2,3,4-tetrahydroquinoline Derivatives

Abstract

Various cis-2-methyl-4-amido-1,2,3,4-tetrahydroquinoline derivatives were synthesized efficiently by reacting aromatic amines and N-vinyl caprolactam or N-vinyl pyrrolidone in the presence of indium trichloride in an aqueous medium in good to excellent yields. These 2,4-disubstituted tetrahydrouinolines showed cis diastereoselectivity.

Keywords:

• Imino Diels–Alder
• indium trichloride
• 2-methyl-4-amido-1,2,3,4-tetrahydroquinolines
• N-vinyllactams
• one-pot

Notes

^a Isolated yields were reported.

^b Reported as gummy material.^{[ 12 ]}