Collect. Czech. Chem. Commun. 2000, 65, 797-804

N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction

Martina Havelková, Martin Studenovský and Dalimil Dvořák*

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


The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alkylhypoxanthine derivatives. Formation of these unexpected products can be rationalised as a Tl+- or Ag+-assisted substitution of halogen with acetate anion. The 6-acetoxypurine derivative thus formed then eliminates ketene and gives 7-benzyl- or 9-benzylhypoxanthine. Conjugate addition of these compounds onto Michael acceptors furnishes the N1-substituted hypoxanthine derivatives.

Keywords: Purines; Hypoxanthines; Heck reaction; Michael additions; Palladium; Thallium acetate.

References: 14 live references.