Highly efficient three-component synthesis of beta-lactams from N-methylhydroxylamine, aldehydes, and phenylacetylene.
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.
Zhao
Liang
L
Department of Chemistry, McGill University, 801 Sherbrooke S. West, Montreal, Québec H3A 2K6, Canada.
Li
Chao-Jun
CJ
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D006898:Hydroxylamines / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis*
D000447:Aldehydes; D006898:Hydroxylamines; D047090:beta-Lactams; C044736:phenylacetylene; D000114:Acetylene; C018338:N-methylhydroxylamine