Categories: Synthesis of N-Heterocycles > Lactams
Synthesis of 3-pyrrolin-2-ones
Recent Literature
A 3 + 2 cycloaddition of α-imino rhodium carbenoids generated from 1-sulfonyl
1,2,3-triazoles with ketene silyl acetals offers a novel and straightforward
synthesis of biologically interesting 3-pyrrolin-2-ones with broad substrate
scope.
R.-Q. Ran, J. He, S.-D. Xiu, K.-B. Wang, C.-Y. Li, Org. Lett., 2014,
16, 3704-3705.
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.
A palladium-catalyzed cyclocarbonylation of propargyl amines in the presence
of benzene-1,3,5-triyl triformate (TFBen) as the CO source and also as the key
promotor provides various substituted 2-oxo-dihydropyrroles in good yields.
J. Ying, Z. Le, X.-F. Wu,
Org. Lett., 2020, 22, 194-198.
Dimethyl sulfoxide (DMSO) and N-iodosuccinimide mediate a metal-free
regioselective 5-exo-dig oxidative cyclization of propargyl-substituted
ynamides via in situ generated enol equivalents. The reaction allows easy access
to functionalized pyrrolidone skeletons. The role of DMSO as oxidant in the
transformation is clarified, and a tentative reaction pathway is proposed.
B. Prabagar, S. Nayak, R. Prasad, A. K. Sahoo, Org. Lett.,
2016, 18, 3066-3069.
A heterocycle-heterocycle interconversion strategy provides 4,5-disubstituted
3-hydroxy-2-pyrrolidinones in good yields. The reported reductive rearrangement approach
especially allows access to unsubstituted 3-hydroxy-2-pyrrolidinone at the
nitrogen position for further functionalization.
P. Kamath, V. Jadhav, M. Lal, Synlett, 2021,
32,
1146-1150.
Conventional approaches for the synthesis of tetramic acid derivatives often
require highly functionalized starting materials and harsh heating conditions in
basic media. A silver-catalyzed strategy enables a mild synthesis of tetramic
acid derivatives from easily available propargylic amines and carbon dioxide in
the presence of DBU.
T. Ishida, R. Kobayashi, T. Yamada, Org. Lett., 2014,
16, 2430-2433.
An unprecedented C(CO)-C(Ar) bond cleavage of β-enaminones under mild and
transition-metal-free conditions followed by 1,3-O/C migration and aerobic
hydroxylation provides various 5-hydroxy-1H-pyrrol-2(5H)-ones with
broad functional group tolerance.
T. Chen, X. Zhang, W. Wang, Y. Feng, Y. Wang, J. Shen, J. Org. Chem.,
2021, 86, 2917-2928.
An efficient sequential halolactamization-hydroxylation reaction of
4-monosubstituted 2,3-allenamides with CuX2 (X = Br, Cl) provides
4-halo-5-hydroxypyrrol-2(5H)-ones in high yields. Halolactamizations of a
fully substituted 2,3-dienamide afforded 4-halo-pyrrol-2(5H)-ones.
S. Ma, H. Xie,
Org. Lett., 2000, 2, 3801-3803.
