Reductive Cyclization of <i>o</i>-Nitrophenyl Propargyl Alcohols:  Facile Synthesis of Substituted Quinolines

Abstract

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.