61537-49-3Relevant articles and documents
(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
, p. 10343 - 10359 (2021/07/31)
(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems
Ichitsuka, Tomohiro,Kobayashi, Shū,Koumura, Nagatoshi,Sato, Kazuhiko,Takahashi, Ikko
, p. 15891 - 15896 (2020/07/13)
Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.
Biphenyl sulfonic acid ligands for catalytic C-N cross coupling of aryl halides with anilines and secondary amines
Wittel, B?rbel,Vogel, Till,Scharl, Heiko,Nerdinger, Sven,Lehnemann, Bernd,Meudt, Andreas,Snieckus, Victor
, p. 4583 - 4593 (2018/07/31)
The use of two biphenyl sulfonic acid ligands for the catalytic C-N cross coupling of aryl halides with anilines, 3-aminopyridine, and secondary amines is reported. Our results represent a significant improvement compared to state of the art methods especially with regards to the removal of palladium.
Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
Roscales, Silvia,Csák?, Aurelio G.
, p. 1667 - 1671 (2018/03/23)
The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
Method for synthesizing diarylamine by optical/nickel concerted catalysis
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Paragraph 0046; 0047; 0048; 0049; 0120; 0121; 0122; 0123, (2018/09/08)
The invention discloses a method for synthesizing diarylamine by optical/nickel concerted catalysis. According to the method, a ligand does not need to be added, and simple and cheap nickel salt is directly used as a metal catalyst to cooperate with a photosensitizer to catalyze arylamine and aryl bromide to generate cross-coupling. The method has the following advantages: (1) the use amount of BODIPY type organic photocatalyst is low, and the BODIPY type organic photocatalyst has a better catalysis effect in comparison with metal iridium and ruthenium photocatalysts reported in the literature; (2) the BODIPY type organic photocatalyst is easy for synthesis; (3) the use amount of nickel salt is few, and the ligand does not need to be added; and (4) the reaction conditions are mild, and theyield of most coupling products is higher than 90%. According to the method disclosed by the invention, high temperature and high pressure equipment is not needed, temperature change scope is small,experimental procedure is simple and easy to operate, and the method has a relatively high application value and industrial popularization potential.
Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones
Bautista, Rafael,Montoya, Pablo A.,Rebollar, Araceli,Burgueno, Eleuterio,Tamariz, Joaquin
, p. 10334 - 10351 (2013/10/22)
A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.
Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols
Maiti, Debabrata,Buchwald, Stephen L.
supporting information; experimental part, p. 17423 - 17429 (2010/03/25)
O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2- cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.
Bioisosteric phentolamine analogs as potent α-adrenergic antagonists
Hong, Seoung-Soo,Bavadekar, Supriya A.,Lee, Sang-Il,Patil, Popat. N.,Lalchandani,Feller, Dennis R.,Miller, Duane D.
, p. 4691 - 4695 (2007/10/03)
The synthesis and biological evaluation of a new series of bioisosteric phentolamine analogs are described. Replacement of the carbon next to the imidazoline ring of phentolamine with a nitrogen atom provides compounds (2, 3) that are about 1.6 times and 4.1 times more potent functionally than phentolamine on rat α1-adrenergic receptors, respectively. In receptor binding assays, the affinities of phentolamine and its bioisosteric analogs were determined on the human embryonic kidney (HEK) and Chinese Hamster ovary (CHO) cell lines expressing the human α1- and α2-AR subtypes, respectively. Analogs 2 and 3, both, displayed higher binding affinities at the α2- versus the α1-ARs, affinities being the least at the α1B- AR. Binding affinities of the methoxy ether analog 2 were greater than those of the phenolic analog 3 at all six α-AR subtypes. One of the nitrogen atoms in the imidazoline ring of phentolamine was replaced with an oxygen atom to give compounds 4 and 5, resulting in a 2-substituted oxazoline ring. The low functional antagonist activity on rat aorta, and binding potencies of these two compounds on human α1A- and α2A-AR subtypes indicate that a basic functional group is important for optimum binding to the α1- and α2A-adrenergic receptors.
Novel alpha adrenergic agents
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, (2008/06/13)
Aspects of the present invention are directed towards compounds of Formula I for the treatment of human erectile disorders including erectile dysfunction in men. wherein: R1 is hydrogen, halo, hydroxy, nitro, cyano, phenyl, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy, carboxy, amino, cyclohexyl, C1-C6 alkylamino, or (C1-C6 alkyl)2amino; R2 is hydrogen, halo, hydroxy, nitro, cyano, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy, carboxy, amino, C1-C6 alkylamino, or (C1-C6 alkyl)2amino; R3 is a group of the formula R4 is hydrogen or C1-C6 alkyl; R5 is hydrogen, halo, hydroxy, nitro, cyano, phenyl, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy, carboxy, amino, C1-C6 alkylamino, or (C1-C6 alkyl)2amino; and R6 is hydrogen, halo, hydroxy, nitro, cyano, trifluoromethyl, C1-C6 alkyl, C1-C6 alkoxy, carboxy, amino, C1-C6 alkylamino, or (C1-C6 alkyl)2amino; or pharmaceutically acceptable salts thereof
