Categories: Synthesis of N-Heterocycles > Lactams >
Synthesis of ε-lactams
Recent Literature
Lewis acid-promoted reactions of alkyl azides with ketones can afford several
products. Cyclohexanones and other cyclic ketones react in the presence of TiCl4
to afford Schmidt-like insertion products, whereas an acid-promoted rearrangement of the azide to an iminium species can occur, mostly with benzylic azides
and TfOH; the iminium species can then be trapped by enolates.
P. Desai, K. Schildknegt, K. A. Agrios, C. Mossman, C. Mossman, G. L.
Milligan, J. Aubé, J. Am. Chem. Soc., 2000,
122, 7226-7232.
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, BF3ˇOEt2-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.
In a metal-free, selective oxidation of cyclic secondary and tertiary amines for
the formation of lactams, molecular iodine facilitates both chemoselective and
regioselective oxidation of C-H bonds directly adjacent to a cyclic amine. The
reaction offers mild conditions, functional group tolerance, and a broad
substrate scope.
R. J. Griffiths, G. A. Burley, E. P. A. Talbot, Org. Lett.,
2017, 19, 870-873.