Halogenierte Pyridine und 1,8‐Naphthyridine. VI

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Abstract
Halogenated pyridines and 1,8‐naphthyridines. VI.The principle of the synthesis of 3‐halomethyl‐2,6‐dichloro‐pyridines has been extended to compounds with side chains of more than one carbon atom in the 3‐position. Feasible synthetic routes are outlined starting from cheap, commercially available α‐methylideneglutaronitrile and trichloroalkyl functional compounds which yield the intermediate 1,3,5‐trisubstituted alkanes. These are cyclized by aqueous mineral acid or by hydrogen bromide in an organic solvent to 2‐substituted glutarimids or hexahydronaphthyridinones, depending on the mode of cyclization. The final aromatization provides a simple route to pyridines or 1, 8‐naphthyridines.