Collect. Czech. Chem. Commun. 2011, 76, 311-326
https://doi.org/10.1135/cccc2011030
Published online 2011-03-17 11:03:00

Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines

Miroslava Tobrmanová, Tomáš Tobrman* and Dalimil Dvořák

Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic

Abstract

C8-Alkenylpurines were synthesized starting from purin-8-yl(allyl) acetates using Pd-catalyzed allylic substitution. The described protocol allows, by reaction of purin-8-yl(allyl) acetates with stabilized nucleophiles, an access to novel (E)-8-alkenylpurine derivatives under Pd2dba3·CHCl3 catalysis in dry THF in yields ranging from 31 to 76%. A wide range of nucleophiles showed exclusive E-alkene formation, however, ethyl nitroacetate gave mixture of E/Z-alkenes. On contrary, purin-2-yl(allyl) acetates reacted smoothly only with dimethyl malonate.

Keywords: Heterocycles; Palladium; Nucleophilic substitution.

References: 50 live references.

This article is part of virtual issue Prof. Pavel Kočovský, FRSE
60th Birthday.