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Synthesis of imidazolidines
Recent Literature
An unprecedented 1,3-dipolar cycloaddition of 1,3,5-triazinanes and
aziridines provides a wide range of functionalized imidazolidine derivatives in
good yields under mild conditions. The reaction is scalable.
L. Tu, Z. Li, T. Feng, S. Yu, R. Huang, J. Li, W. Wang, Y. Zheng, J. Liu, J. Org. Chem., 2019,
84, 11161-11169.
Copper efficiently catalyzes a reaction of N-sulfonylaziridines and
N-alkylanilines in the presence of tert-butyl hydroperoxide to afford
functionalized imidazolidines via nucleophilic ring opening, sp3 C-H
functionalization, and C-N bond formation. The protocol can be used for the
enantiospecific synthesis of imidazolidines with excellent optical purity.
M. Sengoden, A. Bhowmick, T. Punniyamurthy, Org. Lett.,
2017, 19, 158-161.
A visible light-promoted divergent cycloaddition of α-diazo esters to
hexahydro-1,3,5-triazines provides a series of aziridines and imidazolidines in
good yield, by simply changing the reaction media. The reactions occur under
visible light irradiation without photoredox catalysts.
X. Cheng, B.-G. Cai, H. Mao, J. Lu, L. Li, K. Wang, J. Xuan, Org. Lett., 2021, 23,
4109-4114.
A mild one-pot synthesis of highly functionalized
imidazolidines and oxazolidines via SN2-type ring-opening of
activated aziridines and epoxides with amines followed by p-toluenesulfonic acid catalyzed intramolecular cyclization with
aldehydes tolerates a variety of functional groups and furnishes the
desired products in high yields with excellent stereoselectivities.
S. Tarannum, S. Sk, S. Das, I. A. Wani, M. K. Ghorai, J. Org. Chem., 2020, 85,
367-379.
Tungsten hexacarbonyl catalyzes an unprecedented cycloaddition between
acyclic CF3-ketimines and a N-benzyl azomethine ylide to
provide a range of imidazolidines bearing a trifluoromethylated tetrasubstituted
carbon center. This reaction is a rare example of a (2,3) cycloaddition with CF3-ketimines.
Z. Chen, Y. Zhou, T. Hu, H.-Y. Xiong, G. Zhang, J. Org. Chem., 2021, 86,
7552-7562.