104-10-9Relevant articles and documents
p-Tyrosol: a new synthetic method and new types of pharmacological activity
Sysolyatin,Kryukov, Yu. A.,Malykhin,Muradov,Chernysheva,Aliev,Smol’yakova,Anishchenko,Sidekhmenova,Shamanaev, A. Yu.,Plotnikov
, p. 2210 - 2214 (2015)
A new method for the synthesis of p-tyrosol, i.e., 2-(4-hydroxyphenyl)ethanol, has been developed, which considerably simplified the process of preparation of this pharmaceutical substance. The method includes nitration of 2-phenylethanol, catalytic hydrogenation of 2-(4nitrophenyl)ethyl nitrate, and nitrosation of 2-(4-aminophenyl)ethanol, followed by acid hydrolysis of the intermediate diazo compound. The method is easily feasible, furnishes the pharmaceutical substance of high quality, and is quite acceptable for commercialization. Antihypertensive and hemorheologic activities of p-tyrosol in spontaneously hypertensive rats were investigated per se and in combination with captopril. p-Tyrosol in the course administration with captopril was found to enhance the antihypertensive effect of the latter and eliminate its negative effect on red blood cell aggregation.
Nickel-catalyzed formic acid reductions. A selective method for the reduction of nitro compounds
Channe Gowda,Prakasha Gowda,Ramesha Baba,Gowda, Shankare
, p. 2889 - 2895 (2000)
Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and raney nickel. This system is found to be compatible with several sensitive functionalities such as halogens, -OH, -OCH3, -CHO, -COCH3-COC6H5, -COOH, -COOC2H5, -CONH2, -CN, -CH=CH-COOH, -NHCOCH3. The reduction can be carrid out not only with HCOOH but also with HCOONH4.
Thermal dehydration of 2-(4-aminophenyl)ethanol
Schul'Tsev
, p. 2300 - 2303 (2011)
The influence of inorganic nucleophilic agents on the liquid-phase process of thermal dehydration of 2-(4-aminophenyl)ethanol at 200-260°C was investigated. It was found that K2CO3, BaCO3, BaO, CaH2, and NaOH did not catalyze the dehydration, but the process takes place easily with the formation of 4-aminostyrene in high yield, using KOH in the range of 100-180 mol % with respect to 2-(4-aminophenyl)ethanol.
Palladium supported on metal–organic framework as a catalyst for the hydrogenation of nitroarenes under mild conditions
Bao, Lingxiang,Fei, Teng,Li, Jiazhe,Pang, Siping,Sun, Chenghui,Yan, Zhiyuan,Yu, Zongbao
, (2020)
Sustainable development demands an environmentally friendly and efficient method for the hydrogenation of organic molecules, including the hydrogenation of functionalized nitroarenes. In this study, a highly active and selective metal–organic framework-supported palladium catalyst was prepared for the catalytic hydrogenation of nitroarenes. High selectivity (>99%) and excellent yield (98%) of aniline were realized after 2 hours in ethanol under hydrogen (1 atm) at room temperature. The reductions were successfully carried out in the presence of a wide range of other reducible functional groups. More importantly, the catalyst was very stable without the loss of its catalytic activity after five cycles.
Selective reduction of nitro compounds using CeY zeolite under microwaves
Arya, Kapil,Dandia, Anshu
, p. 55 - 58 (2010)
Aliphatic and aromatic nitro compounds were selectively reduced to their corresponding amino derivatives in good yields using formic acid and CeY zeolite under monomode reactor. This system is found to be compatible with several sensitive functionalities. Beside the recycling result showed it had a long catalyst lifetime and could maintain activity even after being used for 20 cycles.
Direct and practical synthesis of primary anilines through iron-catalyzed C-H bond amination
Legnani, Luca,Cerai, Gabriele Prina,Morandi, Bill
, p. 8162 - 8165 (2016)
The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.
Hydrazinium monoformate: A new hydrogen donor. Selective reduction of nitrocompounds catalyzed by commercial zinc dust
Gowda, Shankare,Gowda, B. K. Kempe,Gowda, D. Channe
, p. 281 - 289 (2003)
The nitro group in aliphatic and aromatic nitro compounds also containing reducible substituents such as ethene, nitrile, acid, phenol, halogen, ester, etc., are selectively and rapidly reduced at room temperature to corresponding amines in good yields by employing hydrazinium monoformate, in the presence of commercial zinc dust. It was observed that, hydrazinium monoformate is more effective than hydrazine or formic acid and reduction of nitro group occurs without hydrogenolysis in the low cost zinc dust compared to expensive metals like palladium.
A mild deprotection of trichloroethyl carbamates using indium metal
Mineno, Tomoko,Choi, Seoung-Ryoung,Avery, Mitchell A.
, p. 883 - 886 (2002)
The trichloroethoxycarbonyl moiety was efficiently removed from carbamates to furnish the corresponding amines using indium metal in good to excellent yields.
Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 1618 - 1629 (2021/01/25)
Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
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Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
