Categories: Synthesis of N-Heterocycles >
Synthesis of imidazolidines
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.