Categories: Synthesis of N-Heterocycles, C-N Bond Formation >
Synthesis of lactams and related compounds
| Synthesis of | ||||
 α-Lactams (Aziridinones) |
 β-Lactams |
 γ-Lactams |
 δ-Lactams |
 3-Pyrrolin-2-ones |
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.
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.
An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of
saturated carboxylic esters enables an efficient asymmetric access to lactams
and lactones. The method introduces functional groups at the typically inert
β-sp3 carbons of saturated esters. The use of HOBt as an additive
improves both yields and enantioselectivities of the reactions.
B. Liu, W. Wang, R. Huang, J. Yan, J. Wu, W. Xue, S. Yang, Z. Jin, Y. R. Chi, Org. Lett.,
2018, 20, 260-263.
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