Download PDF
Synthesis 1995; 1995(1): 56-62
DOI: 10.1055/s-1995-3856
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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