Categories: Synthesis of N-Heterocycles, C-N Bond Formation >
Synthesis of lactams and related compounds
| Synthesis of saturated lactams | ||||
 α-Lactams (Aziridinones) |
 β-Lactams |
 γ-Lactams |
 δ-Lactams |
|
Name Reactions
Recent Literature
An oxidative copper-catalyzed arylation of various ring-size lactams with
arylboronic acids gives N-arylated products in good yield without any additional
bases, ligands, or additives.
T. Bathini, V. S. Rawat, B. Sreedhar,
Synlett, 2015, 26, 1348-1351.
A quick, efficient, one-pot, BF3·OEt2-mediated reaction of
various substituted arenes with azido alkanoic acid chlorides affords
substituted N-aryl lactams in good to excellent yields at room
temperature.
D. Caturvedi, A. K. Chaturvedi, N. Mishra, V. Mishra, Synlett, 2012, 23,
2627-2630.
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.
Regioselective ring closing ene-yne metathesis provided an efficient access to
different substituted 1-benzazepine scaffolds. Five- and six-membered lactams
were efficiently prepared by ring-closing metathesis affording highly
functionalizable compounds.
E. Benedetti, M. Lomazzi, F. Tibiletti, J.-P. Goddard, L. Fensterbank, M.
Malacria, G. Palmisano, A. Penoni, Synthesis, 2012, 44,
3523-3533.
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.
After NHC-catalyzed activation of acetic esters, the catalytically generated
triazolium enolate intermediates serve as two-carbon nucleophiles that undergo
highly enantioselective reactions with enones and α,β-unsaturated imines to give
α-unsubstituted δ-lactones and lactams, respectively.
S. Chen, L. Hao, Y. Zhang, B. Tiwari, Y. R. Chi, Org. Lett., 2013,
15, 5822-5825.
 |
New
Routes to Heterocycles |
