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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.
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 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.
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.
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.
