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Chemistry, an Asian journal

Highly efficient three-component synthesis of beta-lactams from N-methylhydroxylamine, aldehydes, and phenylacetylene.


PMID 17441056

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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M50400
N-Methylhydroxylamine hydrochloride, 98%
CH5NO · HCl