89607-23-8Relevant academic research and scientific papers
Synthesis of ureas in the bio-alternative solvent Cyrene
Mistry, Liam,Mapesa, Kopano,Bousfield, Thomas W.,Camp, Jason E.
supporting information, p. 2123 - 2128 (2017/07/24)
Cyrene as a bio-alternative solvent: a highly efficient, waste minimizing protocol for the synthesis of ureas from isocyanates and secondary amines in the bio-available solvent Cyrene is reported. This method eliminated the use of toxic solvents, such as
Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions
Hopkins, Brett A.,Wolfe, John P.
supporting information, p. 9886 - 9890 (2012/10/29)
Positive water effect: A catalyst composed of [Pd2(dba) 3] (dba=dibenzylideneacetone) and (S)-Siphos-PE is effective for the enantioselective coupling of N-allyl ureas with aryl bromides to afford 4-substituted imidazolidin-2-ones. Added water leads to significantly improved enantioselectivities with electron-poor aryl halide substrates. It is suggested that the C-C bond-forming reductive elimination is the enantiodetermining step in these reactions. Copyright
Gold(I)-catalyzed intramolecular hydroamination of N-allylic N′-arylureas to form imidazolidin-2-ones
Li, Hao,Song, Feijie,Widenhoefer, Ross A.
supporting information; experimental part, p. 955 - 962 (2011/06/25)
Treatment of N-allylic N′-arylureas with a catalytic 1:1 mixture of di-tert-butyl-o-biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol%) in chloroform at room temperature led to 5-exo-hydroamination to form the corresponding imidazolidin-2-ones in excellent yield. In the case of N-allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)-catalyzed 5-exo-hydroamination leads to formation of the corresponding trans-3,4-disubstituted imidazolidin-2-ones in excellent yield with ≥50:1 diastereoselectivity.
Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations
Fritz, Jonathan A.,Wolfe, John P.
, p. 6838 - 6852 (2008/09/21)
A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.
A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas
Fritz, Jonathan A.,Nakhla, Josephine S.,Wolfe, John P.
, p. 2531 - 2534 (2007/10/03)
A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one p
SYNTHESIS AND STRUCTURE OF DERIVATIVES OF 2-AMINOOXAZOLINE
Tsoi, L. A.,Salimbaeva, A. D.,Abiyurov, B. D.
, p. 2287 - 2290 (2007/10/02)
2-Alkylamino-5-methyl-1,3-oxazolines and 2-arylimino-5-methyl-1,3-oxazolidines were synthesized by the intramolecular cyclization of allylureas.By comparative analysis of the IR and PMR spectra of model amino and imino compounds it was concluded that the
