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Synthesis of 2,5-Diiodopyrazine by Deprotonative Dimetalation of Pyrazine

Abstract : The deproto-metalation reactions of pyrimidine and pyrazine were regioselectively carried out using lithium tri(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 iodopyrazine in 71 and 63% yields, respectively. The same reaction performed on pyri-dazine afforded a mixture of the 3- and 4-iodo derivatives (55 and 41% yields, respectively). From pyrazine, the 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 1/3).
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Submitted on : Friday, June 27, 2014 - 6:53:50 PM
Last modification on : Thursday, December 12, 2019 - 1:50:21 PM
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Jean-Martial l'Helgoual'Ch, Ghenia Bentabed-Ababsa, Floris Chevallier, Aïcha Derdour, Florence Mongin. Synthesis of 2,5-Diiodopyrazine by Deprotonative Dimetalation of Pyrazine. SYNTHESIS, Georg Thieme Verlag, 2008, pp.4033-4035. ⟨10.1055/s-0028-1083218⟩. ⟨hal-01010345⟩

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