Studies on Tertiary Amine Oxides. XVI. Reactions of Quinoline 1-Oxides with Compounds Containing Reactive Hydrogens in the Presence of Acetic Anhydride.

Abstract

Quinoline 1-oxides were found to react smoothly with compounds containing reactive hydrogens in the presence of acetic anhydride, producing the corresponding 2-substituted quinolines. The yields were generally good to excellent in the reactions of ethyl cyanoacetate, 1, 3-indandione, diethyl malonate, diethyl nitromalonate, ethyl nitroacetate (e. g. ethyl α-cyano-2-quinolineacetate in 88% yield), but acetone, acetophenone or phenylacetonitrile could not enter into the reaction. The reaction of quinoline 1-oxide using benzoyl chloride instead of acetic anhydride and those of pyridine 1-oxides in the presence of acetic anhydride proceeded similarly but in much lower yields.