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Palladium-catalysed Claisen rearrangement of 6-allyloxypurines

Abstract

6-Allyloxypurines readily undergo palladium-catalysed Claisen rearrangement under mild conditions affording N 1-substituted hypoxanthines. In contrast with the previously reported protocol, the Claisen rearrangement can be performed using Pd(PPh3)4 or Pd(dba)2/dppf in dry THF at 60°C. The reaction can accommodate variously substituted allyl fragments to position N 1 of the hypoxanthine skeleton with high yields. Retention of the double bond configuration during rearrangement was observed.

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Correspondence to Tomáš Tobrman.

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Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

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Koukal, P., Dvořáková, H., Dvořák, D. et al. Palladium-catalysed Claisen rearrangement of 6-allyloxypurines. Chem. Pap. 67, 3–8 (2013). https://doi.org/10.2478/s11696-012-0239-y

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  • DOI: https://doi.org/10.2478/s11696-012-0239-y

Keywords

  • Claisen rearrangement
  • purine
  • allyloxypurines
  • palladium
  • hypoxanthine