Palladium-catalysed Claisen rearrangement of 6-allyloxypurines |
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| Authors: | Petr Koukal Hana Dvo?áková Dalimil Dvo?ák Tomá? Tobrman |
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| Institution: | 1. Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic
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| 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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