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Highly Efficient Three‐Component Synthesis of β‐Lactams from N ‐methylhydroxylamine, Aldehydes, and Phenylacetylene
Author(s) -
Zhao Liang,
Li ChaoJun
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600097
Subject(s) - phenylacetylene , chemistry , aldehyde , catalysis , medicinal chemistry , organic chemistry , component (thermodynamics) , physics , thermodynamics
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 β‐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.