A multicomponent coupling sequence for direct access to substituted quinolines.
A titanium-catalyzed three-component coupling reaction can be used to generate tautomers of N-aryl-1,3-diimines. Simple treatment of these products with acetic acid leads to cyclization forming quinoline derivatives in a one-pot procedure. The primary amines employed can be substituted anilines, aminonaphthalenes, or even heterocyclic amines, which leads to a variety of fused-ring heterocyclic frameworks. The one-pot yields varied from 25-71% for the 18 examples presented in this study.
Majumder
Supriyo
S
Michigan State University, Department of Chemistry, East Lansing, Michigan 48823, USA.
Gipson
Kevin R
KR
Odom
Aaron L
AL
D000085:Acetates / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*
D000085:Acetates; D000588:Amines; D011804:Quinolines