13072-69-0Relevant academic research and scientific papers
REACTIONS OF TRIFORMYLMETHANE WITH ADAMANTANE DERIVATIVES CONTAINING PRIMARY AMINO GROUP
Burkhard, Jiri,Arnold, Zdenek
, p. 1947 - 1950 (1992)
Six new compounds were obtained by condensation of triformylmethane with some aminoadamantane derivatives.The study also includes 7-amino-1,3,5-triazaadamantane.
Catalytic hydration of cyanamides with phosphinous acid-based ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights
álvarez, Daniel,Cadierno, Victorio,Crochet, Pascale,González-Fernández, Rebeca,López, Ramón,Menéndez, M. Isabel
, p. 4084 - 4098 (2020/07/09)
The synthesis of a large variety of ureas R1R2NC(O)NH2 (R1 and R2 = alkyl, aryl or H; 26 examples) was successfully accomplished by hydration of the corresponding cyanamides R1R2NCN using the phosphinous acid-based complexes [MCl2(η6-p-cymene)(PMe2OH)] (M = Ru (1), Os (2)) as catalysts. The reactions proceeded cleanly under mild conditions (40-70 °C), in the absence of any additive, employing low metal loadings (1 molpercent) and water as the sole solvent. In almost all the cases, the osmium complex 2 featured a superior reactivity in comparison to that of its ruthenium counterpart 1. In addition, for both catalysts, the reaction rates observed for the hydration of the cyanamide substrates were remarkably faster than those involving classical aliphatic and aromatic nitriles. Computational studies allowed us to rationalize all these trends. Thus, the calculations indicated that the presence of a nitrogen atom directly linked to the CN bond depopulates electronically the nitrile carbon by inductive effect when coordinated to the metal center, thus favouring the intramolecular nucleophilic attack of the OH group of the phosphinous acid ligand to this carbon. On the other hand, the higher reactivity of Os vs. Ru seems to be related with the lower ring strain on the incipient metallacycle that starts to form in the transition state associated with this key step in the catalytic cycle. Indirect experimental evidence of the generation of the metallacyclic intermediates was obtained by studying the reactivity of [RuCl2(η6-p-cymene)(PMe2OH)] (1) towards dimethylcyanamide in methanol and ethanol. The reactions afforded compounds [RuCl(η6-p-cymene)(PMe2OR)(NCNMe2)][SbF6] (R = Me (5a), Et (5b)), resulting from the alcoholysis of the metallacycle, which could be characterized by single-crystal X-ray diffraction. This journal is
Method for continuous production of adamantanamine hydrochloride
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Paragraph 0017-0021, (2019/01/24)
The invention aims to provide a method for continuous production of adamantanamine hydrochloride by a high-temperature kneading/spiral propelling reactor. In comparison with a traditional batch reactor, the reaction equipment is small in size and has good reaction stability, helps improve production efficiency by continuous reaction production of amantadine products and more importantly helps avoid the temperature runaway problem of the system, and has good safety. The invention has the prominent characteristics as follows: by using the high-temperature kneading/spiral propelling reactor as the reaction equipment, an aminolysis material can be continuously produced, retention time of the aminolysis material in the equipment can be controlled, side effects are reduced, and the aminolysis material can be removed out of the equipment periodically; in the feeding process, dramatic temperature rise of the system is avoided; and under the condition of high reaction yield, the equipment is small in size, is safe and simple to operate, and has good industrial application value.
Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation
Wu, Fan,Alom, Nur-E,Ariyarathna, Jeewani P.,Na?, Johannes,Li, Wei
supporting information, p. 11676 - 11680 (2019/07/31)
A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.
One-Pot Amination of Cage Hydrocarbons
Leonova,Skomorokhov,Moiseev,Klimochkin
, p. 1703 - 1709 (2016/02/03)
A one-pot procedure has been proposed for the synthesis of amines directly from cage hydrocarbons. A number of cage amines have been synthesized by treatment of adamantane, its homologs, and structurally related cage hydrocarbons with nitric acid in acetic acid and subsequent addition of urea and heating.
Adamantylation and adamantylalkylation of amides, nitriles, and ureas in trifluoroacetic acid
Shokova,Musulu, Tasula,Luzikov,Kovalev
, p. 844 - 856 (2007/10/03)
A new preparative procedure was developed for N-adamantylation of carboxylic acids amides and ureas, and C5-adamantylation of barbituric acid in trifluoroacetic acid medium with tertiary adamantanols and 1-adamantylalkanols. The reaction of 2-adamantanols and secondary 1-adamantylalkanols with nitriles was for the first time used in the preparation of W-(2-adamantyl)-and N-(1-adamantylalkyl)amides.
Adamantylation and adamantylalkylation of amides, nitriles and ureas in trifluoroacetic acid
Shokova, Elvira,Mousoulou, Tasoulla,Luzikov, Yurij,Kovalev, Vladimir
, p. 1034 - 1040 (2007/10/03)
A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.
