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■ 1,3-Dipolar Cycloaddition Reactions of Benzonitrile Oxide to 2(1H )-Pyrazinone and Its N - and O - Methyl Derivatives

Antonino Corsaro,* Ugo Chiacchio, Venerando Pistarà, and Giancarlo Perrini

*Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, I-95125 Catania, Italy

Abstract

2(1H)-Pyrazinone, which is in equilibrium with 2-pyrazinol, reacts with benzonitrile oxide (BNO) affording the N₁-adduct with a 67% yield, while 2-methoxypyrazine gives two methoxypyrazinones (ca. 3%) and a biscycloadduct together with its degradation product, which derive from the two unisolable monocycloadducts to the C=N₄ double bond. N-Methylpyrazinone gives only the degradation product (3.4%) of the initial monocycloadduct of BNO to C=N₄ double bond.