Abstract
A new methodology based on the Eschenmoser coupling reaction has been developed for the preparation of quinoline anhydro bases. Its application has allowed the synthesis of 4-alkylidene-N-methylquinolines in two steps from N-methyl-4-quinolinethione (1) via appropriately 4-thiosubstituted quinolinium salts. Starting from 4(1H)-quinolinethione (6) itself, this process, combined with the Menschutkin reaction, is further demonstrated by the preparation of variously N-substituted 4-alkylidenequinolines. It is believed this route should provide access to pyridine and other quinoline anhydro bases.
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