87976-13-4Relevant academic research and scientific papers
N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature
Abha Saikia, Raktim,Barman, Dhiraj,Dutta, Anurag,Jyoti Thakur, Ashim
, p. 400 - 410 (2020/12/17)
Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver
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.
Regioselective multicomponent sequential synthesis of hydantoins
Olimpieri, Francesca,Bellucci, Maria Cristina,Marcelli, Tommaso,Volonterio, Alessandro
, p. 9538 - 9555 (2013/01/16)
The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry. The Royal Society of Chemistry 2012.
Synthesis of new imidazolidinones, spiro-imidazolidinones and spiro-hydantoins
Chande, Madhukar S.,Balel, Satish K.
, p. 377 - 380 (2007/10/03)
α-Alkyl/aryl-α-arylaminopropionitriles (1) and 1-arylamino-1-cyano-cyclohexanes/cyclopentanes (5) react with alkyl/arylisocyanates to afford new imidazolidinones (2, 3) and spiro-imidazolidinones (6, 7) respectively. Compounds 2 and 6 on hydrolysis give hydantoins (4) and spiro-hydantoins (8), respectively.
Reactions of diazoalkanes with isocyanates. Synthesis of imidazolidine-2,4-diones, oxindoles, and oxazolidinones
Fulton, Janet B.,Warkentin, John
, p. 1177 - 1184 (2007/10/02)
Thermolysis of a 5,5-dialkyl-Δ3-1,3,4-oxadiazolin-2-one in nitrobenzene containing an aryl isocyanate at 150 deg C affords a 1,3-diaryl-5,5-dialkyl imidazolidine-2,4-dione, an N-arylcarbamoyl-3,3-dialkyloxindole, and a 3-aryl-2-arylimino-5,5-dialkyl-1,3-oxazolidin-4-one.Those products arise from attack of a diazoalkane, generated in situ from the oxadiazolinone by thermal cycloreversion, on the isocyanate function.Two imidazolidine diones, three oxazolidinones, and 14 oxindoles were prepared.
Synthesis and Some Reactions of 2-Imino-2,5-dihydro-1,3,4-thiadiazoles. Formation of β-Lactams
Yamamoto, Iwao,Abe, Ikuo,Nozawa, Muneharu,Kotani, Mitsuhiro,Motoyoshiya, Jiro,et al.
, p. 2297 - 2301 (2007/10/02)
The title compounds, 2-imino-2,5-dihydro-1,3,4-thiadiazoles (2a-c), were prepared by oxidation of thiosemicarbazones.The reactions of (2a-c) with ketenes gave the spiro-β-lactams (7a-d), via cycloaddition.On the other hand, the reaction of (2a) with phenyl isocyanate gave the thiohydantoins (9) and (10).The reactions of compound (2) with some other nucleophiles are also described.
