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Appl. Chem. Vol. 74, No. 8, pp.
Pure and Applied
Vol. 74, Issue 8
Development of a general process for the synthesis of highly
Joseph Sisko** and Mark Mellinger
Synthetic Chemistry, GlaxoSmithKline, 709 Swedeland
Road, P.O. Box 1539, UW2820, King of Prussia, PA 19406-0939, USA
Abstract: Several highly substituted imidazoles have
been under investigation at GlaxoSmithKline as potential therapies for
the treatment of rheumatoid arthritis and have spawned the need for
a general synthetic method for their preparation on a multikilogram
scale. We describe herein the optimization of a general method for the
preparation of aryl-substituted TosMIC reagents and the ease with which
they undergo [3+2] cycloadditions with a host of imines, prepared in
situ, to generate densely functionalized imidazoles with various substitution
patterns in a completely regioselective manner.
** Corresponding author.
* Plenary lecture presented at the 3rd Florida Conference
on Heterocyclic Chemistry (FloHet-III), Gainesville, Florida, USA, 6-8
March 2002. Other lectures are published in this
issue, pp. 1317–1368.
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