Studies towards the decarboxylative cross-coupling of Azole-4-carboxylic acids.
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Date
26/11/2015Item status
Restricted AccessEmbargo end date
31/12/2100Author
Stephen, Jennifer
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Abstract
Some interesting, biologically active natural products have been found to contain
poly-azole fragments within their core. These fragments are linked through the 2-
position of one azole and the 4-position of its neighbour. Decarboxylative cross-coupling methodology may provide a route to these desired
linked azoles through cross-coupling of azole-4-carboxylic acids with azole-2-
halides or with azoles containing no substitution at the 2-position.
Investigations into the silver-mediated decarboxylation, and subsequent coupling
potential, of thiazole and oxazole-4-carboxylic acids are reported. Methods towards
the synthesis of novel chlorinated thiazole and oxazole acids and their precursors are
also described.
A method to successfully couple these acids to aryl iodides has been developed and
the scope of this reaction extended to a variety of functionalised azole-4-carboxylic
acids. Attempts to extend this methodology and combine the decarboxylative coupling with
CH activation of a second azole are also described.