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The dipolar cyclo­addition of methyl acrylate to 1,5,6-trimethyl-3-oxidopyrazinium

✍ Scribed by Helliwell, Madeleine ;You, Yun ;Joule, John A.

Publisher
International Union of Crystallography
Year
2006
Tongue
English
Weight
199 KB
Volume
62
Category
Article
ISSN
1600-5368

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✦ Synopsis

5,6-Dimethylpyrazin-2-one reacts with iodomethane to give a quaternary salt, deprotonation of which liberates a 3-oxidopyrazinium which undergoes a 1,3-dipolar cycloaddition with methyl acrylate to form methyl 5,8-dimethyl-4-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-6-exo-carboxylate, C~11~H~16~N~2~O~3~, as the major product.

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✍ Kyukwan Zong; Seung Il Shin; Dong Ju Jeon; Jung No Lee; Eung K. Ryu 📂 Article 📅 2000 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 273 KB

## Abstract 3‐Aryl‐4‐methoxycarbonylisoxazoles were prepared from the reaction of a variety of substituted benzonitrile oxides with methyl 3‐(__p__‐nitrobenzoyloxy)acrylate in moderate to good yields.