Synlett 2007(14): 2217-2221  
DOI: 10.1055/s-2007-984918
LETTER
© Georg Thieme Verlag Stuttgart · New York

Improved and Practical Procedures for the Preparation of Highly Substituted Pyridines and Pyridazines via Silica-Mediated Aromatisation

Nicola Catozzia, William J. Bromleya, Pierre Wasnairea, Mairi Gibsonb, Richard J. K. Taylor*a
a Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
b Neurology & GI CEDD, GlaxoSmithKline R&D, New Frontiers Science Park, Harlow CM19 5AW, UK
Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
Further Information

Publication History

Received 27 April 2007
Publication Date:
23 July 2007 (online)

Zoom Image

Abstract

A new and straightforward procedure is described for the preparation of highly substituted pyridines and pyridazines. The method involves a Diels-Alder/retro-Diels-Alder sequence leading to dihydropyridine or related intermediates, which can be aromatized to pyridines and pyridazines by treatment with silica gel. The value of this procedure has been demonstrated with a one-step ­synthesis of an E-ring-modified steroid.

Crossref Cited-by logo
Article Citations