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Synthesis of lactams and related compounds

Synthesis of











Name Reactions

Biginelli Reaction

Recent Literature

The reaction of amide and thioamide dianions with epibromohydrin resulted in regioselective formation of 5-(hydroxy­methyl)pyrrolidin-2-ones (pyroglutaminols) and -thiones.
I. Freifeld, H. Armbrust, P. Langer, Synthesis, 2006, 1807-1808.

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.

Optically enriched N-fused bicyclic amides and small- and medium-ring unsaturated cyclic amines can be synthesized in up to 98% ee through Mo-catalyzed desymmetrization of readily available achiral polyene substrates. The effects of catalyst structure, olefin substitution, positioning of Lewis basic functional groups and ring size are examined and discussed in detail.
E. S. Sattely, G. Alexander Cortez, D. C. Moebius, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc., 2005, 127, 8526-8533.

ROM-RCM of cyclobutenylmethylamines having an alkyne moiety in a tether afforded isoquinoline derivatives in good yields using a second-generation Grubbs catalyst.
M. Mori, H. Wakamatsu, K. Tonogaki, R. Fujita, T. Kitamura, Y. Sato, J. Org. Chem., 2005, 70, 1066-1069.

Organic azides are easily and chemoselectively reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions. γ-Azidonitriles give pyrrolidin-2-imines in an outstanding cyclization.
L. Benati, G. Bencivenni, R. Leardini, D. Nanni, M. Minozzi, P. Spagnolo, R. Scialpi, G. Zanardi, Org. Lett., 2006, 8, 2499-2502.

New Routes to Heterocycles
Preparation of Cyclic Amines

C-N Ring-forming Reactions by Transition Metal-catalyzed Intramolecular Alkene Hydroamination