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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 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.


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.