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Synthesis of imidazolidinones and related compounds
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An efficient, versatile and practical gram-scale preparation of
oxazolidinone, imidazolidinone and dioxolanone is achieved.
N. Alouane, A. Boutier, C. Baron, E. Vrancken, P. Mangeney, Synthesis, 2006, 860-864.
A nickel-catalyzed cycloaddition of aziridines with isocyanates proceeded
smoothly to give iminooxazolidine derivatives in good yields. A longer
reaction time allowed the isomerization of the iminooxazolidine to the
corresponding imidazolidinone derivatives.
T. Munegumi, I. Azumaya, T. Kato, H. Masu, S. Saito, Org. Lett.,
2006, 8, 379-382.
A functional-group-tolerant and scalable cobalt-catalyzed cyclization of
alkenyl carbamates and alkenyl isoureas provides common five- and
six-to-eight-membered cyclic carbamates and ureas via transition-metal hydrogen
atom transfer and radical-polar crossover.
T. Nagai, N. Mimata, Y. Terada, C. Sebe, H. Shigehisa,
Org. Lett., 2020, 22, 5522-5527.
The combined use of photocatalysis with careful engineering of the substrate
enables C-H amination forming imidazolidinones and related nitrogen heterocycles
from readily accessible hydroxylamine precursors. Preliminary mechanistic
results are consistent with the formation of free carbamoyl triplet nitrenes as
reactive intermediates.
R. A. Ivanovich, D. E. Polat, A. M. Beauchemin,
Org. Lett., 2020, 22, 6360-6364.
Imidazolidin-2-ones are prepared in two steps from readily available N-allylamines.
Addition of the amine starting materials to isocyanates affords N-allylureas,
which are converted to imidazolidin-2-ones with generation of two bonds and
up to two stereocenters in the presence of aryl bromides, a catalytic amount
of Pd2(dba)3/Xantphos and NaOtBu.
J. A. Fritz, J. S. Nakhla, J. P. Wolfe, Org. Lett.,
2006, 8, 2531-2534.
An oxidation of imidazolinium, imidazolium and benzimidazolium derivatives in the presence
of copper and air provides imidazolidinones, imidazolones, and benzimidazolones
in good yields under mild conditions. Low yields were obtained with sterically
hindered substrates.
D. Li, T. Ollevier,
Org. Lett., 2019, 21, 3572-3575.
An efficient Pd-catalyzed asymmetric allylic cycloaddition of readily accessible
nitrogen-containing allylic carbonates to isocyanates provides imidazolidinones
and tetrahydropyrimidinones with high yields and high levels of
enantioselectivities.
I. Khan, B. H. Shah, C. Zhao, F. Xu, Y. J. Zhang,
Org. Lett., 2019, 21, 9452-9456.
2-Vinylaziridines undergo cycloaddition reactions with various
heterocumulenes in the presence of Pd(OAc)2 and PPh3 at
room temperature to afford five-membered ring products regioselectively in good
yields.
D. C. D. Butler, G. A. Inman, H. Alper, J. Org. Chem., 2000,
65, 5887-5890.
The use of di-t-butyldiaziridinone as
nitrogen source and a N-heterocyclic carbene-Pd(0) complex as catalyst
allows an efficient diamination of a wide
variety of conjugated dienes and trienes in good
yields with high regio- and stereoselectivities.
L. Xu, H. Du, Y. Shi, J. Org. Chem.,
2007,
72, 7038-7041.
A wide variety of terminal olefins can be effectively diaminated at allylic and
homoallylic carbons via formal C-H activation in good yields with high
stereoselectivity using di-tert-butyldiaziridinone as nitrogen source and
Pd(PPh3)4 as catalyst.
H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc., 2007,
129, 7496-7497.
Pd-catalyzed sequential hydroaminations of readily available 1,3-enynes
provide a broad scope of imidazolidinones, thiadiazolidines, and
imidazolidines. Asymmetric sequential hydroamination generates a series of
synthetically valuable, enantioenriched imidazolidinones.
Q. Li, X. Fang, R. Pan, H. Yao, A. Lin, J. Am. Chem. Soc.,
2022, 144, 11364-11376.
The phosphazene base BEMP catalyzes an intramolecular hydroamidation of
propargylic ureas to provide imidazolidin-2-ones and imidazol-2-ones with
excellent chemo- and regioselectivities under ambient conditions and short
reaction times.
A. Casnati, A. Perrone, P. P. Mazzeo, A. Bacchi, R. Mancuso, B. Gabriele, R.
Maggi, G. M. E. Motti, A. Stirling, N. Della Ca', J. Org. Chem., 2019, 84,
3477-3490.
A palladium-catalyzed intramolecular diamination reaction yields cyclic
ureas as direct products of an oxidative alkene transformation in the
presence of iodosobenzene diacetate as terminal oxidant.
J. Streuff, C. H. Hövelmann, M. Nieger, K. Muniz, J. Am. Chem. Soc.,
2005, 127, 14586-14587.