3157-03-7Relevant academic research and scientific papers
Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides
Wang, Chuan-Chuan,Qu, Ya-Li,Liu, Xue-Hua,Ma, Zhi-Wei,Yang, Bo,Liu, Zhi-Jing,Chen, Xiao-Pei,Chen, Ya-Jing
, p. 3546 - 3554 (2021/02/16)
The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.
Method for synthesizing N - substituted hydantoin compounds (by machine translation)
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Paragraph 0063-0068, (2020/11/22)
The invention discloses a synthetic method of N - substituted hydantoin compounds, which comprises the following steps: taking an acyl azide compound shown as a formula I and a glycine ethyl ester compound as shown in a formula II as a raw material, carrying out heating reaction under the presence of an additive to obtain N - substituted hydantoin compounds as shown in formula III. In the formula, R1 And R2 Independently selected from hydrocarbyl, substituted hydrocarbyl, aryl, substituted aryl or aralkyl; R2 Selected from hydrocarbyl or aryl; R3 Selected from a hydrogen atom and a hydrocarbyl group. To the synthesis method, the functionalized N - substituted hydantoin compounds can be efficiently synthesized, the synthesis steps are few, the conditions are mild, the operation is safe, the raw materials are nontoxic, cheap and easily available, and the synthesis method has the N - substituted hydantoin compounds with the nitrogen heterocyclic skeleton with novel structure, the yield can reach 92%, the purity is 99%, and industrial synthesis is easy. (by machine translation)
Copper-Mediated N-Arylations of Hydantoins
Thilmany, Pierre,Gérard, Phidéline,Vanoost, Agathe,Deldaele, Christopher,Petit, Laurent,Evano, Gwilherm
, p. 392 - 400 (2018/12/11)
A set of two broadly applicable procedures for the N-arylation of hydantoins is reported. The first one relies on the use of stoichiometric copper(I) oxide under ligand- A nd base-free conditions and enables a clean regioselective arylation at the N3 nitrogen atom, while the second one is based on the use of catalytic copper(I) iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine and promotes arylation at the N1 nitrogen atom. Importantly, the combination of these two procedures affords a straightforward entry to diarylated hydantoins.
Palladium-catalyzed synthesis of substituted hydantoins - A new carbonylation reaction for the synthesis of amino acid derivatives
Beller, Matthias,Eckert, Markus,Moradi, Wahed A.,Neumann, Helfried
, p. 1454 - 1457 (2007/10/03)
One-step synthesis of substituted hydantoins can be achieved by the palladium-catalyzed 'ureidocarbonylation' of aldehydes with urea derivatives and carbon monoxide [Eq. (1)]. This surprisingly selective protocol converts substituted ureas into 1,5- and 1,3,5-substituted hydantoins in yields of up to 93 %.
Silver(I) ion-mediated desulfurization-cyclization of isothiocyanates with several hydroxy acids and N-substituted amino acids
Shibuya, Isao,Goto, Midori,Shimizu, Masao,Yanagisawa, Masaru,Gama, Yasuo
, p. 2667 - 2673 (2007/10/03)
The title reaction of 2-hydroxy-2-methylpropionic acid with phenyl isothiocyanate gave 5,5-dimethyl-3-phenyl-2,4-oxazolidinedione. The structure was determined by X-Ray crystal analysis, and the reaction pathway was estimated. The reactions of other 2-hyd
Generation and Reactivity of N,N-Dimethylaminobenzotriazolylcarbene a New Nucleophilic Carbene
Katritzky, Alan R.,Cheng, Dai,Leeming, Peter,Ghiviriga, Ion,Hartshorn, Chris M.,Steel, Peter J.
, p. 1935 - 1941 (2007/10/03)
N,N-Dimethylaminobenzotriazolylcarbene (5) reacted with phenyl isocyanate in a [1+2+2] cycloaddition and then with nucleophiles to generate various hydantoins 10 in a one-pot procedure. It was also found that this novel carbene reacted with trans-dibenzoylethylene (11) in a [1+4] cycloaddition, generating 2-dimethylamino-3-benzoyl-5-pbenylfuran (13) and 2-phenyl-3-[benzotriazol-1-y1]-4-benzoylfuran (14) whose structures were confirmed by 1H-13C long range correlations as well as the structure of furan 14 being confirmed by X-ray crystallography.
BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID
Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
, p. 375 - 390 (2007/10/02)
Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.
