Reductive cyclization of o-nitrophenyl propargyl alcohols: facile synthesis of substituted quinolines.
Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively. Tertiary propargyl alcohols gave excellent yields of the quinoline derivative, while the yields of quinolines were slightly reduced when secondary propargyl alcohol derivatives were utilized.
Sandelier
Matthew J
MJ
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
DeShong
Philip
P