Collect. Czech. Chem. Commun. 2006, 71, 1221-1228

Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives

Martin Klečka, Tomáš Tobrman and Dalimil Dvořák*

Department of Organic Chemistry, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic


6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

Keywords: Purines; Cross-coupling reactions; Palladium; Grignard reagent; Copper; Allylic rearrangement.

References: 31 live references.