13114-89-1Relevant academic research and scientific papers
N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor
Yadav, Mangal S.,Singh, Sumt K.,Agrahari, Anand K.,Singh, Anoop S.,Tiwari, Vinod K.
, p. 2494 - 2502 (2021/03/26)
A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.
Synthetic method and application of urea compound
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Paragraph 0032-0034; 0036, (2019/06/07)
The invention relates to a synthetic method of a urea compound, comprising the following steps: adding substituted oxazolone and sodium acetate into a methanol solution, and adding substituted amine under the stirring condition, reacting and carrying out column chromatography to obtain the urea compound. The defect that dangerous compounds need to be used during existing synthetic process is overcome, and a one-pot method is adopted to replace an existing reaction with low yield. The method of the invention has mild reaction condition, the operation is simple, raw materials are easily available, and the substrate can be converted into various other useful molecules. The compound has strong practicality, and can be applied to synthesis of the pesticide daimuron, dieresis long and the anti-cancer drug Sorafenib. The invention relates to a green and environmentally-friendly unsymmetrical urea compound synthesis method with simple process and low cost.
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.
supporting information, p. 17824 - 17832 (2016/11/18)
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.
Imidazolin-2-iminato Ligand-Supported Titanium Complexes as Catalysts for the Synthesis of Urea Derivatives
Naktode, Kishor,Das, Suman,Bhattacharjee, Jayeeta,Nayek, Hari Pada,Panda, Tarun K.
supporting information, p. 1142 - 1153 (2016/02/09)
The reactions of tetrakis(dimethylamido)titanium(IV) [Ti(NMe2)4] with three different imidazolin-2-imines (ImRNH; R = tert-butyl (tBu), mesityl (Mes), and 2,6-diisopropylphenyl (Dipp)) afforded the corresponding titanium i
Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation
Clayden, Jonathan,Turner, Hazel,Pickworth, Mark,Adler, Thomas
, p. 3147 - 3150 (2007/10/03)
(Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on el
Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines
Adler, Thomas,Bonjoch, Josep,Clayden, Jonathan,Font-Bardia, Merce,Pickworth, Mark,Solans, Xavier,Sole, Daniel,Vallverdu, Lluis
, p. 3173 - 3183 (2007/10/03)
N-Acylated 2-substituted anilines undergo slow Ar-N bond rotation, allowing in some cases isolation of enantiomeric or diastereoisomeric atropisomers and in others the determination of the rate of Ar-N bond rotation by NMR. 2-Iodoanilides bearing a branch
THE INTRAMOLECULAR NH...Cl HYDROGEN BOND IN UREA DERIVATIVES CONTAINING THE o-CHLOROPHENYL GROUP
Mido, Yoshiyuki,Okuno, Tomoko
, p. 29 - 34 (2007/10/02)
The solution ν(N-H) vibrations of various disubstituted ureas containing a halophenyl group have been examined in order to directly confirm the presence of an intramolecular NH...Cl hydrogen bond in the o-chloro analog.In chlorophenyl derivatives the ν(N-
