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Synthesis 1997; 1997(8): 949-952
DOI: 10.1055/s-1997-1289
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The Synthesis of Thienopyridines from ortho-Halogenated Pyridine Derivatives; Part 2

D. H. Bremner1 , A. D. Dunn2 , K. A. Wilson3 , K. R. Sturrock3 , G. Wishart3
  • 1University of Abertay Dundee, Department of Molecular and Life Sciences, Bell Street, Dundee DD1 1HG, Scotland, Fax +44(1382)308663; E-mail: d.h.bremner@tay.ac.uk
  • 2Beilstein-Institut, Carl-Bosch-Haus, Varrentrappstraße 40-42, D-6000 Frankfurt/Main 90, Germany
  • 3University of Abertay Dundee, Department of Molecular and Life Sciences, Bell Street, Dundee DD1 1HG, Scotland
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Publication History

Publication Date:
31 December 2000 (online)

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Synthetic routes to the ortho-halogenated pyridine derivatives, ethyl 2- and 4-chloro-3-pyridylacetate, ethyl 3-bromo-4-pyridylacetate and ethyl 3-bromo-2-pyridylacetate, which have methylene groups activated by the ester functionality are reported. Reaction of these pyridines with carbon disulfide in the presence of sodium hydride, followed by quenching with iodomethane, results in the formation of the corresponding thienopyridines in moderate yields.

thienopyridines - ortho-halogenation - pyridines - base-catalysed cyclisation