4-methyl-2-imidazolidinone

The organometallic sensitizer can be replaced by a purely organic dye such as eosin Y that acts as a photoredox catalyst after excitation with visible light and gives rise the more stable triplet state [26]. In the presence of eosin Y and MacMillan s trons-methyl imidazolidinone catalyst 10 and substrates (aldehyde and a-bromocarbonyl compounds) the alkylation reaction performed similarly while requiring somewhat longer reaction times at the optimal -5 °C temperature. 

Imidazolidin-2-one, l-(5-nitro-2-thiazolyl)-pharmacological activity, 6, 328 Imidazolidin-4-one, l-aryl-3-phenyl-2-thioxo- C NM S, 355 Imidazolidinones C NMR, 5, 355 Imidazolidin-2-ones nucleophilic displacement, 5, 428 polymers, 1, 279-280 reactivity, 5, 376 synthesis, 5, 466, 471 Imidazolidin-4-ones synthesis, 5, 468 Imidazoline, 2-alkyl-synthesis, 5, 463 Imidazoline, 2-amino-applications, 5, 498 Imidazoline, 2-aryl-synthesis, 5, 463 Imidazoline, 2-methyl-synthesis, 5, 487 Imidazoline, 2-nitroamino-synthesis, 5, 471 2-Imidazoline, 2-arylamino-tautomerism, 5, 368 2-Imidazoline, 1-benzyl-methylation, 5, 425 2-Imidazoline, 1,2-diaryl-synthesis, 5, 463... 

Chemical name l-[(6-Chloro-3-pyridinyl)methyl]-2-imidazolidinone... 

Nelson SD, Breck GD, Trager WF. In vivo metabolite condensations. Formation of Nl-ethyl-2-methyl-N3-(2,6-dimethylphenyl)-4-imidazolidinone from the reaction of a metabolite of alcohol with a metabolite of lidocaine. J Med Chem 1973 16(10) 1106-1112. 

Allenamides are more stable and hence easier to handle in synthetic manipulations [152], When allenamide 187 was heated with 2equiv. of acrolein or methyl vinyl ketone (MVK), cycloadducts were isolated as single regioisomers. Allenamides containing either an oxazolidinone or imidazolidinone moiety also reacted with these a,/1-unsaturated carbonyl compounds under thermal conditions. 

Imidazolidinone 0-tosyloxime 6k was also reported to react with alkyl and aryl Grignard reagents in good yields (Scheme 65). The resulting iV-organylimines can be hydrolyzed with CsOH to afford primary amines and/or reduced with LiAlH4 to A-methyl secondary amines. 

Azoniabicyclo[3.2.2]nonane nitrate N, A -Diacetyl-A, A -dinitro-1,2-diaminoethane Diaminoguanidinium nitrate l,3-Dinitro-2-imidazolidinone A, A -Dinitro-A -methyl-1,2-diaminoethane l,3,6,8-Tetraazoniatricyclo[6.2.1. U jdodecane tetranitrate l,3,5,7-Tetranitroperhydro-l,3,5,7-tetrazocine Triaminoguanidinium nitrate Triaminoguanidinium perchlorate... 

A hot solution of 180 g (1.18 mol) of (S)-a-hydroxybenzeneacetic acid (mandelic acid) in 300 mL of acetone (distilled from calcium chloride) is added to a hot stirred solution of 180 g (1.15 mol) of rac-2- tcrt-buty 1 -3-methyl-4-imidazolidinone in 100 mL of acetone. After seeding and stirring, the solution is allowed to cool down very slowly to 4 °C by insulating the flask. The crystals formed are filtered off and suspended in 290 mL of acetone and stirred under reflux for 1 h. After cooling, filtering and redissolving in 170 mL of acetone as above, the crystals formed on cooling are collected to yield the (S)-imidazolidinone (S)-mande-late yield 108 g (30%) mp 115.5-116.5 °C [a]D +89 (c = 1, ethanol). 

Experimental details for the preparation of l-acyl-2-re77-butyl-3-methyl-4-imidazolidinones are given below. 

To 238 mmol of the rra 5-5-alkyl-2-tert-butyl-3-methyl-4-imidazolidinone 7 (R1 = CH3) are added 65.9 g (302 mmol) of di-terr-butyl dicarbonate and 2.8 g (22.9 mmol) of 4-(dimethylamino)pyridine in 400 mL of acetone with cooling. After 8 h at 20 °C, 32.4 mL (232 mmol) of triethylamine are added and, after 2 h of stirring, 20 mL of water is added and the mixture is stirred for a further 2 h. After evaporation of the acetone, the residue is extracted with diethyl ether and the organic phase is washed with two 100-mL... 

The general alkylation procedure for imidazolidinones (vide supra) is employed, however, 2 mol equivalents of base have to be used for the imidazolidine acids. (2S,4,S )-3-Benzoyl-2-rw-butyl-1 -methyl-5-oxo-4-imidazo-lidineacetic acid is not soluble in THE and is added to the solution of the base (in this case lithium diethylamide in THF/hexane) as a suspension in THF, followed by enolate formation at 0°C and recooling to — 78 "C before adding an excess of the haloalkanc (often 5- 10 mol equivalents). See Table 4 for specific examples. 

Methyl-1,3-diisopropylpseudourea, 170 Methylene compounds, nitrosation of, 395 4-Methylene-2-imidazolidinones, 140 4-Methylene-2-oxazolidinones, 140 2-Methyl-5-ethylpyridine, 96... 

The predicted low enantiocontrol from reactions performed with methallyl diazoacetate (Eq. 5.18) was borne out in reactions catalyzed by Rh2(MEPY)4 and Rh2(MEOX)4, but when chiral imidazolidinone-ligated dirhodium(II) was used, enantioselectivity rose to 89% ee (Table 5.8) [89]. The use of CuPF6/7b also caused relatively high enantiocontrol (87% ee) [92] which, however, decreases to 82% ee when the methyl group of 36 was replaced by n-butyl, whereas with Rh2(4S-MPPIM)4 the enantiopurity of the product corresponding to 37 was 93% ee. The A-3-phenylpropanoyl substituents of Rh2(4S-MPPIM)4 help to create a more conformationally restrictive environment that leads to enhanced enantiocontrol. 

Ichikawa et al. reported on the synthesis and antifungal activity of l-[(lfJ,2fi)-2-(2,4-difluorophenyl)-2-hydroxy-l-methyl-3-(l//-l,2,4-triazol-Tyl)propyl]-3-[4-(l//-l-tetrazolyl)phenyl]-2-imidazolidinone 597. Compound 597 was selected as an injectable candidate for clinical trials based on the results of evaluations of solubility, stability, hemolytic effect, and in vivo antifungal activities <2001CPB1102, 2001CPB1110>. 

The mixture of 4.9 g of 2-(2-tosyloxyethyl)-l,4-benzodioxan, 2.54 g of l-(4-piperidyl)-2-imidazolidinone, 5.0 g of anhydrous sodium carbonate and 100 ml of 4-methyl-2-pentanone is stirred and refluxed for 3 days. It is filtered, evaporated, to yield the l-[l-[2-(l,4-benzodioxan-2-yl)-ethyl]-4-piperidyl]-2-imidazolidinone, melting point 125°C, (recrystallized from isopropanol). 

Chemical Name 4-Imidazolidinone, 2-imino-3-methyl-l-phenyl-Common Name Azolimine Structural Formula ... 

Imazalil heterocyclic nitrogen, imidazole Imazamethabenz-methyl heterocyclic nitrogen, imidazolidinone... 

The data of the NMR spectra of l- [(5-nitro-l,3,4-thiadiazol-2-yl)methylen]-amino -2-imidazolidinone [540], 2-[(2-methyl-5-nitrothiazol-4-yl)methylene]-malonate and its imidazole analogs [547, 548] have been reported. 

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