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Paper | Regular issue | Vol 65, No. 5, 2005, pp.1079-1097
Published online, 4th March, 2005
DOI: 10.3987/COM-05-10342
Reactions of Benzonitrile Oxide with Methoxypyrimidines and Pyrimidones

Antonino Corsaro,* Venerando Pistarà, Antonio Rescifina, Maria A. Chiacchio, Anna Piperno, and Giovanni Romeo

*Department of Chemical Sciences, University of Catania, Viale Andrea Doria 6, 95125 Catania, Italy

Abstract

Methoxypyrimidines preferentially add to benzonitrile oxide to give cycloadducts to their C=N double bonds. These, however, lose benzonitrile affording the corresponding pyrimidones. Cycloadditions to their C=C double bonds take place to a very low extent, and products generally undergo a ring opening process which affords the corresponding oximes. Pyrimidones preferentially give addition products to their nitrogen atoms, and only in the case of 4-pyrimidone, the cycloadduct to its C=C double bond was isolated.