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DOI: 10.1055/s-0028-1083218
Synthesis of 2,5-Diiodopyrazine by Deprotonative Dimetalation of Pyrazine
Publication History
Publication Date:
06 November 2008 (online)

Abstract
The deproto-metalation reactions of pyrimidine and pyrazine were regioselectively carried out using lithium tris(2,2,6,6-tetramethylpiperidino)cadmate in tetrahydrofuran at room temperature. This result was demonstrated by subsequent trapping with iodine to afford 4-iodopyrimidine and 2-iodopyrazine in 71% and 63% yields, respectively. The same reaction performed on pyridazine afforded a mixture of the 3- and 4-iodo derivatives (55% and 41% yields, respectively). From pyrazine, access to the 2,5-diiodo derivative (40% on a 25 mmol scale) proved possible using a larger amount of base (1 equiv instead of 0.33).
Key words
metalations - cadmium - lithium - heterocycles - iodine
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