Palladium-catalysed Claisen rearrangement of 6-allyloxypurines

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(PPh 3 ) 4 or Pd(dba) 2 /dppf in dry THF at 60°C. The reac...

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Bibliographic Details
Published inChemical papers Vol. 67; no. 1; pp. 3 - 8
Main Authors Koukal, Petr, Dvořáková, Hana, Dvořák, Dalimil, Tobrman, Tomáš
Format Journal Article
LanguageEnglish
Published Heidelberg SP Versita 2013
Versita
Subjects
allyloxypurines
Biochemistry
Biotechnology
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Claisen rearrangement
hypoxanthine
Industrial Chemistry/Chemical Engineering
Materials Science
Medicinal Chemistry
Original Paper
palladium
purine
palladium
Claisen rearrangement
allyloxypurines
hypoxanthine
purine
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Summary: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(PPh 3 ) 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.
ISSN:0366-6352
1336-9075
1336-9075
DOI:10.2478/s11696-012-0239-y