35305-46-5Relevant academic research and scientific papers
Synthesis method of substituted urea compound
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Paragraph 0034-0039; 0078-0083, (2021/03/31)
The invention discloses a synthesis method of a substituted urea compound, which comprises the following steps: stirring aldehyde, N-aryl urea, trichlorosilane and Lewis base in an organic solvent ata temperature range of -20 DEG C to room temperature for
Facile synthesis of phthalidyl fused spiro thiohydantoins through silica sulfuric acid induced oxidative rearrangement of ninhydrin adducts of thioureas
Mandal, Subhro,Pramanik, Animesh
, (2019/12/24)
A one-pot three-component sequential synthetic protocol produces structurally and biologically important phthalidyl fused spiro N,N′-disubstituted thiohydantoins from readily available aromatic isothiocyanates, primary amines and ninhydrin. In this three-step synthesis while the initial two steps are catalyst-free, in the final step silica sulfuric acid (SSA) induces an oxidative rearrangement in [3.3.0]-bicyclic 1,2-diol adducts of ninhydrin and thioureas under solvent-free condition to generate the final products spiro-fused thiohydantoins. The adequate acidity of SSA in cooperation with moderate oxidizing property promotes a facile oxidative rearrangement in 1,2-diol intermediates to produce the spiro-fused thiohydantoins with diverse functionalities. Easy recyclability of SSA, good to excellent yield of the products, wider substrate scope, shorter reaction time, solvent-free two steps out of three and high atom economy make this method attractive and practicable.
An easy access to unsymmetrical ureas: A photocatalytic approach to the Lossen rearrangement
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
, p. 24498 - 24503 (2014/07/07)
An efficient and operationally simple method for the synthesis of unsymmetrical ureas from various hydroxamic acids and amines has been developed. Plausibly, the protocol involves visible-light-initiated in situ formation of Vilsmeier-Haack reagent and COBr2 with CBr4 and a catalytic amount of DMF in the presence of Ru(bpy)3Cl2 as a photocatalyst to bring about the Lossen rearrangement at room temperature. the Partner Organisations 2014.
Iron(III) catalysed synthesis of unsymmetrical di and trisubstituted ureas - A variation of classical Ritter reaction
Basavaprabhu, Hosamani,Sureshbabu, Vommina V.
, p. 2528 - 2533 (2012/04/23)
An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties. The Royal Society of Chemistry 2012.
Parallel synthesis of ureas and carbamates from amines and CO2 under mild conditions
Peterson, Scott L.,Stucka, Sabrina M.,Dinsmore, Christopher J.
supporting information; experimental part, p. 1340 - 1343 (2010/06/15)
"Chemical Equation Presented" A mild and efficient library synthesis technique has been developed for the synthesis of ureas and carbamates from carbamic acids derived from the DBU-catalyzed reaction of amines and gaseous carbon dioxide. Carbamic acids derived from primary amines reacted with Mitsunobu reagents to generate isocyanates in situ which were condensed with primary and secondary amines to afford the desired ureas. Similarly, carbamic acids from secondary amines reacted with alcohols activated with Mitsunobu reagents to form carbamates.
NEW FLUOROUS TAGGING AND SCAVENGING REACTANTS AND METHODS OF SYNTHESIS AND USE THEREOF
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Page 58, 59, 61, 62, (2008/06/13)
The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation. The chemical transformations result in a second fluorous tagged organic compound wherein the fluorous nature of the second fluorous tagged organic compound can then be reduced by removing the fluorous group therefrom, thereby producing a second organic compound that may be employed as a pharmaceutical compound or intermediate, or a combinatorial library component.
Fluorous electrophilic scavengers for solution-phase parallel synthesis
Zhang, Wei,Chen, Christine Hiu-Tung,Nagashima, Tadamichi
, p. 2065 - 2068 (2007/10/03)
A fluorous isatoic anhydride and isocyanate are synthesized and used as scavengers for amines in solution-phase parallel synthesis of urea, thiourea, and β-hydroxyamine analogs. The resulting fluorous derivatives are readily separated from the reaction mi
Kinetics and mechanism of the aminolysis of p-nitrophenyl N-phenylcarbamates
Koh, Han Joong,Kim, Ok Sun,Lee, Hai Whang,Lee, Ikchoon
, p. 725 - 730 (2007/10/03)
Kinetic studies of the reactions of p-nitrophenyl N-phenylcarbamates with benzylamines were carried out in acetonitrile at 25·0°C. Second-order (k2) and third-order (k3) rate constants were observed for all the Y-substituted carbamates except for Y=m Cl. The relatively large magnitude of ρx (for X-substituted benzylamines) and ρY together with a positive cross-interaction constant ρxy supports a stepwise mechanism involving rate-limiting breakdown of the zwitterionic tetrahedral intermediate T±. Kinetic isotope effect studies with deuterated benzylamine (XC6H4CH2ND2) indicate that in the base-catalyzed path, k3, rate-limiting deprotonation occurs at the amino group of benzylamine within the T± intermediate. The low ΔH≠ and ΔS≠ values for the k3 process are in accord with the proposed mechanism.
ARYLMETHYL ISOCYANATES
Kozhushko, B. N.,Lomakina, A. V.,Paliichuk, Yu. A.,Shokol, V. A.
, p. 654 - 660 (2007/10/02)
Chloromethyl isocyanate reacts readily with aromatic hydrocarbons in the presence of anhydrous ferric chloride or other catalysts of the Friedel-Crafts reaction with the formation of arylmethyl isocyanates.The latter add alcohols and amines readily, being converted into the corresponding substituted urethanes and ureas.When heated in the presence of catalytic amounts of 1,3-dimethylphosphol-3-ene they give substituted carbodiimides.
