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Updated: Jul 15, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Highly efficient three-component synthesis of beta-lactams from N-methylhydroxylamine, aldehydes, and phenylacetylene
1Department of Chemistry, McGill University, 801 Sherbrooke S. West, Montreal, Québec H3A 2K6, Canada.
Abstract:
The three-component reaction of N-substituted hydroxylamines, aldehydes, and phenylacetylene catalyzed by CuCl/2,2'-bipyridine in the presence of NaOAc under neat conditions afforded the corresponding beta-lactams in good to excellent yields. Aromatic, heteroaromatic, and aliphatic aldehydes are tolerated in this reaction. The electronic effects of the aldehydes were studied for the reaction with N-methylhydroxylamine and N-benzylhydroxylamine. For N-methylhydroxylamine, electron-rich aldehydes provided higher yields than electron-deficient aldehydes, whereas for N-benzylhydroxylamine, no significant electronic effect was observed for the aldehydes.
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