Reactions of Quinoline and 4-Chloroquinoline 1-Oxides with Phenoxyacetonitrile, Chloromethylphenylsulfone, and Methylthiomethyl-p-tolylsulfone

1 January 1987

journal article
research article
Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES

Vol. 25 (1) , 229-233
https://doi.org/10.3987/s-1987-01-0229

Abstract

Quinoline and 4-chloroquinoline 1-oxides react with phenoxyacetonitrile (1) and chloromethylphenylsulfone (3) in KOH-DMSO and in t-BuOK-THF to give the respective vicarious nucleophilic substitution products, 2-cyanomethyl-(2a and 2b) and 2-phenylsulfonylmethylquinoline 1-oxides (4a and 4b). The reactions with methylthiomethyl-p-tolylsulfone (5) afford not only the vicarious nucleophilic substitution products (6a and 6b) but also the products by means of hydride elimination (7a and 7b).

Keywords

HETEROCYCLES

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