Categories: Synthesis of N-Heterocycles > Lactams >
Synthesis of δ-lactams
Recent Literature
A palladium-catalyzed intramolecular hydroamidation of amidoalkynes in
1,4-dioxane at 100°C gives lactams in good yields.
N. T. Patil, Z. Huo, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem., 2006, 71, 3612-3614.
Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles
affords α-alkyl lactims. Subsequent mild, acidic hydrolysation gives the
corresponding α-alkyl-δ-amino esters hydrochloride salts. Neutralisation of
these salts with base results in smooth intramolecular cyclisation to afford
α-alkyl lactams in excellent yield.
P. J. M. Taylor, S. D. Bull, P. C. Andrews, Synlett,
2006, 1347-1350.
N-Alkenyl β-ketoamides undergo a mild cyclization in the presence of
Au[P(t-Bu)2(o-biphenyl)]Cl and AgOTf with excellent regioselectivities and
yields. The reaction provides an efficient method to prepare highly substituted
lactams.
C.-Y. Zhou, C.-M. Che, J. Am. Chem. Soc., 2007,
129, 5828-5829.
A very simple method for the α-arylation of N-protected
2-piperidinones in high yield is described. Key factors are the use of ZnCl2 and
Pd(dba)2 and the nature of the base.
A. de Filippis, D. G. Pardo, J. Cossy, Tetrahedron, 2004,
60,
9757-9767.
An intramolecular vinylation of various iodoenamides using CuI as the
catalyst and N,N'-dimethylethylenediamine as the ligand led to five-
to seven-membered lactams in moderate to excellent yields.
T. Hu, C. Li, Org. Lett., 2005, 7, 2035-2038.
A direct Pd-catalyzed arylation reaction for the intramolecular formation of
biaryl compounds using a novel phosphine ligand offers enhanced catalytic
activity for transformations of previously unreactive substrates.
L.-C. Campeau, M. Parisien, M. Leblanc, K. Fagnou, J. Am. Chem. Soc.,
2004, 126, 9186-9187.
