Categories: C-N Bond Formation >
Synthesis of imides
Related |
 |
 |
 |
Recent Literature
A convenient, efficient, and selective N-Alkylation of N-acidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. In this
manner, phthalimide, indole, benzimidazole, and succinimide can be successfully
alkylated.
Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004,
208-212.
An efficient and simple method enables the N-alkylation of aromatic cyclic
imides using cesium carbonate as the base in anhydrous N,N-dimethylformamide
at low temperatures (20-70˚C). The employment of microwave irradiation presents
noteworthy advantages over conventional heating. The method is compatible with
base labile functional groups.
M. I. Escudero, L. D. Kremenchuzky, I. A. Perillo, H. Cerecetto, M. M. Blanco, Synthesis, 2011,
571-576.
Copper acetate promoted N-arylation of imides with boronic acids can be employed
as a major method for the synthesis of N3-aryl hydantoins.
H. M. Hügel, C. J. Rix, K. Fleck, Synlett, 2006,
2290-2292.
In a one-pot cascade transformation of ketones into α-imidoketones, N-bromosuccinimide
(NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and
diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a nucleophilic
promoter for the activation of NBS. α-Bromination is supposed as the key step in
the process.
Y. Wei, S. Lin, F. Liang, Org. Lett., 2012,
14, 4202-4205.
An oxo-amination process with readily available N-bromosuccinimide (NBS)
and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the
oxidant provides amino alcohols in a single step. For the first time, the
formation of reactive Me2S+-O-Br species generated by the
interaction of NBS with DMSO has been proven.
P. K. Prasad, R. N. Reddi, A. Sudalai, Org. Lett., 2016, 18,
500-503.
In a palladium-catalyzed intermolecular aminocarbonylation of alkenes, the use
of hypervalent iodine reagent can accelerate the reaction. The current
transformation presents a convenient method to generate β-amino acid derivatives
from simple alkenes.
J. Cheng, X. Qi, M. Li, P. Chen, G. Liu, J. Am. Chem. Soc., 2015,
137, 2480-2483.
AgBF4 or InBr3/AgBF4 (1:3) as catalyst and
N-halophthalimide as both nitrogen and halogen source enable a simple, efficient,
and highly atom economic haloamidation of simple alkenes. A broad range of
olefins afford vicinal haloamines in good yields and with high regioselectivity
and diastereoselectivity.
L. Song, S. Luo, J.-P. Cheng, Org. Lett., 2013,
15, 5702-5705.
TBAI as catalyst and TBHP as oxidant enable a metal-free cross-coupling of
enamines and electron-deficient amines through oxidative C(sp2)-N
bond formation. This efficient organocatalytic synthesis of synthetically useful
diaminoalkene derivatives features readily available starting materials and wide
substrate scope.
Y. Yuan, W. Hou, D. Zhang-Negrerie, K. Zhaou, Y. Du, Org. Lett.,
2014,
16, 5410-5113.