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Synthesis 1995; 1995(1): 56-62
DOI: 10.1055/s-1995-3856
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New and Facile Synthesis of Mono- and Bifunctional N-Substituted 4-Alkylidenequinolines by an Eschenmoser Approach

Jocelyne Levillain, Michel Vazeux*
  • *Laboratoire de Chimie des Composés Thioorganiques, URA CNRS 480, ISMRA, Université de Caen, 6 Bd Maréchal Juin, 14050 CAEN Cedex, France
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Publication Date:
31 December 2000 (online)

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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.

Menschutkin reaction - Eschenmoser sulfide contraction - quinoline bases - quinolinium salts - quinoline anhydro bases

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