Nucleophilic Substitution of 4-Chloroguinoline 1-Oxide and Related Compounds by Means of Hydride Elimination

Abstract

The reaction of 4-chloroquinoline 1-oxide (A) with pinacolone and &-BuOK in +-BuNH2 at -10~-15'C gives 4-chloro-2-pinacolylquinoline 1-oxide in good yield by means of hydrideelimination.Similar reactions of A with acetone, 2-butanone, acetophenonerand ethyl andt-htyl acetates occur when treated with t-BuOK or n-BuLi in 5-BuNH2 at -1 0 ~-1 5 ~C , or c-BuOK, KNH2 or -NaNH2 in liq NH3 at -70°C.Reactions of this type proceed also with quinoline 1-oxide (2).3-bromoquinoline 1-oxide (A), p-chloronitrobenzene (4) and nitrobenzene.In order to examine the possibility of the nucleophilic substitution of 4-chloro-2 quinoline 1-oxide (A) by means of ArSRNl mechanism , we tried the potassium sbutoxide (g-Bu0K)-catalyzed reaction of &with pinacolone in e -b u t y l a m i n e (g-