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Paper | Regular issue | Vol 38, No. 10, 1994, pp.2199-2204
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6795
N-1 Oxidation of Adenine Substituted at N-9 by an Olefinic Chain

René Beugelmans,* André Lechevallier, Rachid Benhida, Tawfik Gharbaoui, and Angela Morris

*Institut des Chimie des Substances Naturelles, C.N.R.S., Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


The oxidation of 9-vinyladenine derivatives (1a-c) with m-chloroperoxybenzoic acid (MCPBA) leads selectively to the corresponding N-1 oxides (2a-c) and when the 6-amino group is protected, the oxidation occurs in the double bond of the olefinic chain to give the epoxides (6a, b) selectively.