Base-promoted reactions of α-halogeno-alkylanilides

Abstract

Hydride-promoted reactions of 2-halogeno-alkylcarboxanilides afford heterocyclic and acyclic condensation products, some of the latter compounds arising upon hydrolysis and/or rearrangement of the former ones. Competitive formation of dioxopiperazines versus oxazolidinone derivatives or their transformation products depends mainly upon the nature (primary, secondary or tertiary) of the halide moiety. Concurrent dehydrohalogenation of 2-bromo-isobutyranilides leads to unsaturated condensation products.