101-42-8Relevant articles and documents
A novel procedure for the formation of isatins via carbonylation of lithiated N'-aryl-N,N-dimethylureas
Smith, Keith,El-Hiti, Gamal A.,Hawes, Anthony C.
, p. 945 - 947 (1999)
Isatin and substituted isatins can be formed in very good yields from the appropriate N'(2-bromoaryl)-N,N-dimethylureas via bromine-lithium exchange followed by treatment with carbon monoxide.
Selenium-catalyzed reductive carbonylation of nitrobenzene with amines as coreagents to give unsymmetric phenylureas
Yang, Ying,Lu, Shiwei
, p. 4845 - 4846 (1999)
The reductive carbonylation of nitrobenzene catalyzed by selenium to yield unsymmetric phenylureas has been studied. When secondary amines were used as coreagents, a single product, PhNHCONR2, was formed; when primary amines were chosen as coreagents, mixed products, including RNHCONHR, RNHCONHPh and PhNHCONHPh, were obtained.
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Kaufmann et al.
, p. 385,394 (1970)
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Substitution reaction of N,N'-diphenylurea by amines to unsymmetric phenylureas
Yang, Ying,Lu, Shiwei
, p. 559 - 561 (1999)
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Mazzocchi,Rao
, p. 957,958 (1972)
Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex
Bhattacharjee, Jayeeta,Das, Suman,Kottalanka, Ravi K.,Panda, Tarun K.
, p. 17824 - 17832 (2016)
The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.
Facile dehalogenation of halogenated anilines and their derivatives using Al-Ni alloy in alkaline aqueous solution
Weidlich, Tomas,Prokes, Lubomir
, p. 590 - 597 (2011)
This article describes the simple hydrodehalogenation of halogenated anilines and their derivatives by the action of Raney aluminium-nickel alloy in aqueous alkaline solution at room temperature. The reaction course was monitored by means of 1H nuclear magnetic resonance (NMR) spectroscopy and GC-MS spectra. The effect of Al and Ni and the nature and quantity of the base for effective hydrodehalogenation were studied. The possibility of lowering Al content more than 500 times and Ni content more than 10 times in the filtered mother liquor by a dehalogenation procedure was tested using precipitation. The reduction method described was satisfactorily proved for dehalogenation of polyhalogenated anilines in the multiphase dimethoxymethane/aqueous NaOH/Al-Ni reaction mixture. Dehalogenation under multi-phase conditions was demonstrated for the preparation of ortho-alkylated anilines from simply available 2-substituted-4-chloroanilines. Versita Sp. z o.o.
Photochemical transformation of aqueous para-halogenophenylureas: Evidence for the intermediary formation of carbenes
Boukhram,Richard
, p. 849 - 851 (2000)
N-Substituted 4-iminocyclohexa-2,5-dienylidenes (λ(max) = 300 and 405 nm) are detected at pulse end upon laser flash photolysis of aqueous monuron and metobromuron. In oxygenated medium these carbenes are converted into N-substituted iminoquinone-O-oxides
Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions
Zhu, Xiancui,Xu, Mengchen,Sun, Jinrong,Guo, Dianjun,Zhang, Yiwei,Zhou, Shuangliu,Wang, Shaowu
, p. 5213 - 5218 (2021/10/19)
Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.
Reaction of N-methylazomethine ylide with aroyl azides: Synthesis of imidazolidin-4-ones
Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
, p. 773 - 776 (2019/02/13)
Aryl isocyanates generated in situ from aroyl azides react with N-methylazomethine ylide generated in situ from N-methylspiroanthraceneoxazolidine at 210 °C in a microwave reactor to form 3-arylimidazolidin-4-ones in 30–81% yield.
