cas 6312-87-4, N-(4-PHENOXY-PHENYL)-ACETAMIDE

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A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
supporting information
p. 1955 - 1958
(2021/03/02)

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
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Paragraph 0134-0138; 0140

(2021/05/29)

Synthesis, structure-activity relationship and molecular docking studies of novel quinoline-chalcone hybrids as potential anticancer agents and tubulin inhibitors
A new series of quinoline-chalcone hybrids was synthesized. The structures of these compounds were characterized by spectroscopic methods including 1H and 13CNMR and mass spectroscopy. The cytotoxic activity of compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma) and A2780/RCIS (Cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), MCF-7/MX (Mitoxantrone resistant human breast cancer cells) and normal Huvec cells. The structure-activity relationship of synthesized compounds is discussed. Among quinolines 5e, 5g and 5j possessing benzoyl group showed significant cytotoxic activity against both resistant cancer cells and their parents. Compounds 5g and 5j, demonstrated the most antiproliferative activity with IC50 values ranging from 2.32 to 22.4 μM. They were also identified as tubulin inhibitors and induced cell cycle arrest at G2/M phase and apoptosis. Compound 5j induced more arrest at G2/M phase in four cancer cell lines compared to compound 5g. Finally, molecular dynamics simulation and molecular docking studies of compound 5j into the colchicine-binding site of tubulin demonstrated the possible interaction of this compound in the active site of tubulin.
Mirzaei, Salimeh,Hadizadeh, Farzin,Eisvand, Farhad,Mosaffa, Fatemeh,Ghodsi, Razieh
(2019/11/26)

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism
Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.
Tang, Li,Wang, Zhi-Lv,He, Yan-Hong,Guan, Zhi
p. 4929 - 4936
(2020/08/21)

Visible-light-induced Beckmann rearrangement by organic photoredox catalysis
A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.
Tang, Li,Wang, Zhi-Lv,Wan, Hai-Lan,He, Yan-Hong,Guan, Zhi
supporting information
p. 6182 - 6186
(2020/09/01)

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
supporting information
p. 4911 - 4915
(2019/07/31)

Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions
The direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions has been developed. The reported protocol is practical and represents an efficient method to produce functionalized amides in moderate to good yields.
Xiong, Biquan,Wang, Gang,Xiong, Tao,Wan, Liming,Zhou, Congshan,Liu, Yu,Zhang, Panliang,Yang, Changan,Tang, Kewen
supporting information
p. 3139 - 3142
(2018/07/13)

A to aryl diazonium tetrafluoroborate salts with a nitrile preparation machine acid radical amine compounds (by machine translation)
The invention provides a high-efficiency, high-selective synthesis of different substituted functional group containing organic amide compound, it adopts the cuprous iodide as a catalyst, in order to aryl diazonium tetrafluoroborate salts compounds and organic nitrile compound as the reaction substrate, the reaction system by adding the organic solvent, water and alkali. The advantage of this method: cheap and easily obtained catalyst; the substrate has a high applicability; mild reaction conditions, safe and reliable; the resulting target product selectivity is close to 100%, yield is as high as 90% or more. The method solves the traditional synthetic organic amide compound of rigorous reaction conditions, the reaction selectivity is poor, the experimental procedure is complicated, the productivity is low and needs to be used for the environment of a harmful reagent and the like, it has good industrial application prospect. The invention also provides a corresponding different substituted functional group containing organic amide compound. (by machine translation)
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Paragraph 0042

(2018/06/04)

Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment
Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.
Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
p. 105 - 116
(2016/01/20)

Indole and indazole compounds as an inhibitor of cellular necrosis
The present invention refers to a formula (1) compounds of, pharmaceutically acceptable salts or isomers thereof thereof, and characterized by by containing as active ingredients-associated diseases, cell death and method for the prevention or treatment of relates and compositions. [Formula 1] In formula said R 1, R 2, R 3, R 4, R 5, R 6, A, X, n and m to equal the specification.
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Paragraph 0340; 0341

(2016/10/08)

Metal-free n -arylation of secondary amides at room temperature
The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.
Tinnis, Fredrik,Stridfeldt, Elin,Lundberg, Helena,Adolfsson, Hans,Olofsson, Berit
supporting information
p. 2688 - 2691
(2015/06/16)

Pd-Catalyzed C-H activation/oxidative cyclization of acetanilide with norbornene: Concise access to functionalized indolines
An efficient Pd-catalyzed oxidative cyclization reaction for the synthesis of functionalized indolines by direct C-H activation of acetanilide has been developed. The norbornylpalladium species formed via direct ortho C-H activation of acetanilides is supposed to be a key intermediate in this transformation. This journal is the Partner Organisations 2014.
Gao, Yang,Huang, Yubing,Wu, Wanqing,Huang, Kefan,Jiang, Huanfeng
supporting information
p. 8370 - 8373
(2014/07/22)

Picolinamides as effective ligands for copper-catalysed aryl ether formation: Structure-activity relationships, substrate scope and mechanistic investigations
The use of picolinic acid amide derivatives as an effective family of bidentate ligands for copper-catalysed aryl ether synthesis is reported. A fluorine-substituted ligand gave good results in the synthesis of a wide range of aryl ethers. Even bulky phenols, known to be very challenging substrates, were shown to react with aryl iodides with excellent yields using these ligands. At the end of the reaction, the first examples of end-of-life Cu species were isolated and identified as CuII complexes with several of the anionic ligands tested. A preliminary mechanistic investigation is reported that suggests that the substituents on the ligands might have a crucial role in determining the redox properties of the metal centre and, consequently, its efficacy in the coupling process. An understanding of these effects is important for the development of new efficient and tunable ligands for copper-based chemistry.
Sambiagio, Carlo,Munday, Rachel H.,Marsden, Stephen P.,Blacker, A. John,McGowan, Patrick C.
supporting information
p. 17606 - 17615
(2015/02/05)

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides
2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling of aryl halides with various phenols under mild conditions. The catalytic system shows great functional-group tolerance and excellent reactive selectivity.
Qiu, Yatao,Jia, Weijun,Yao, Zhiyi,Wu, Fanhong,Jiang, Sheng
p. 1502 - 1510
(2013/05/08)

Metal-free arylation of oxygen nucleophiles with diaryliodonium salts
Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright
Jalalian, Nazli,Petersen, Tue B.,Olofsson, Berit
supporting information
p. 14140 - 14149,10
(2012/12/12)

A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions
A new bulky biarylphosphine ligand (L8) has been developed that allows the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions than previously possible. A direct correlation between the size of the ligand substituents in the 2′, 4′, and 6′ positions of the nonphosphine containing ring and the reactivity of the derived catalyst system was observed. Specifically, the rate of coupling increased with the size of these substituents.
Salvi, Luca,Davis, Nicole R.,Ali, Siraj Z.,Buchwald, Stephen L.
supporting information; experimental part
p. 170 - 173
(2012/03/08)

Palladium-catalyzed C-H aminations of anilides with N - fluorobenzenesulfonimide
The first amide-directed, palladium-catalyzed, intermolecular, highly selective C-H aminations with the non-nitrene-based nitrogen source N-fluorobenzenesulfonimide have been developed. This methodology might provide a new pathway for directed metal-catalyzed aromatic C-H amination.
Sun, Kai,Li, Yan,Xiong, Tao,Zhang, Jingping,Zhang, Qian
supporting information; experimental part
p. 1694 - 1697
(2011/04/17)

Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts
A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky ortho-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, racemization-prone amino acid derivatives, and heteroaromatics are also tolerated. The methodology is expected to be of high utility in the synthesis of complex molecules and in the pharmaceutical industry.
Jalalian, Nazli,Ishikawa, Eloisa E.,Silva, Luiz F.,Olofsson, Berit
supporting information; experimental part
p. 1552 - 1555
(2011/04/26)

Efficient iron/copper-cocatalyzed o-arylation of phenols with bromoarenes
Low catalytic amount CuI and Fe(acac)3 were found to effectively promote the C-O cross-coupling reaction in the presence of K2CO 3 as the base. A serious of diaryl ethers with different substitutents can be synthesized in good to excellent yields. This efficient and economic method is attractive for applications on an industrial scale. Georg Thieme Verlag Stuttgart New York.
Liu, Xiaoyan,Zhang, Songlin
supporting information; experimental part
p. 268 - 272
(2011/03/20)

INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.
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Page/Page column 12

(2010/08/08)

INDOLE AND INDAZOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
The present invention relates to indole or indazole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole or indazole compounds as an active ingredient.
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Page/Page column 42

(2009/04/25)

(2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides
(Chemical Equation Presented) Employing (2-pyridyl)acetone as a new supporting ligand, the copper-catalyzed coupling reactions of aryl chlorides, aryl bromides, and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. This reaction displays great functional groups compatibility and excellent reactive selectivity.
Zhang, Qi,Wang, Deping,Wang, Xianyang,Ding, Ke
supporting information; experimental part
p. 7187 - 7190
(2009/12/09)

Copper-catalyzed one-pot multicomponent coupling reaction of phenols, amides, and 4-bromphenyl iodide
(Chemical Equation Presented) An efficient copper-catalyzed multicomponent reaction of phenols, amides, and 4-bromphenyl iodide was developed that uses commercially available N,N-dimethylglycine as the ligand. This multicomponent reaction proceeds in moderate to good yields for a range of phenols and amides. The simple experimental procedure and high levels of functional group compatibility make this method attractive for applications on pesticides.
Chen, Wenming,Li, Jianjun,Fang, Dongmei,Feng, Chun,Zhang, Chenggang
supporting information; experimental part
p. 4565 - 4568
(2009/05/27)

Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids
An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl inflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
Liu, Zhijian,Larock, Richard C.
p. 3198 - 3209
(2007/10/03)

Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
(Chemical Equation Presented) A variety of diaryl ethers were synthesized by the Pd-catalyzed reaction of (hetero)-aryl halides and phenols. These reactions were achieved through the use of two new di-tert-butylphosphino biaryl ligands that overcome several limitations of previously described methods.
Burgos, Carlos H.,Barder, Timothy E.,Huang, Xiaohua,Buchwald, Stephen L.
p. 4321 - 4326
(2007/10/03)

Method of producing organic compounds in presence of oxyethylene ether catalyst and in a solvent minimized environment
A process of producing organic compounds, such as acetaminophen, nitroalcohols and indoles, employs a catalyst system of an oxyethylene ether and a metal containing inorganic or organic reagent. The oxyethylene ether at least partially complexes the metal of the inorganic or organic reagent. As such, the reactions may be conducted neat. The processes are environmentally friendly and operationally simple.
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Page 6-7

(2008/06/13)

Catalysis of the Photo-Fries Reaction: Antibody-Mediated Stabilization of High Energy States
A conformationally constrained hapten is presented that is capable of catalyzing the first antibody-mediated photo-Fries rearrangement. In this reaction, absorption of light energy by a diphenyl ether substrate results in homolytic C-O bond cleavage followed by recombination to yield biphenyl-derived products. The most proficient antibody studied converts 4-phenoxyaniline 15 into 2-hydroxy-5-aminobiphenyl 16 under high-intensity irradiation at a rate of 8.6 μM/min. These results support a recent hypothesis stating that immunization with conformationally constrained haptens provides higher titers for the acquisition of simple binding antibodies; however, in this case, conformational constraint does not ensure the development of more efficient catalysts. Using the obtained antibodies, the presence of products resulting from escape of free radicals from the solvent cage can be suppressed, altering the excited state energy surface such that free radicals are funneled into the formation of the desired biphenyl product. However, studies also show the inactivation of the antibodies as a result of photodecay of the biphenyl product. Using an isocyanate scavenging resin, the photodecay product could be removed and the inactivation of the antibody drastically reduced. Furthermore, despite the observed photodecay, turnover of the antibody was present; this represents the first case in which true turnover of a photochemical reaction using a catalytic antibody could be observed.
Dickerson, Tobin J.,Tremblay, Martin R.,Hoffman, Timothy Z.,Ruiz, Diana I.,Janda, Kim D.
p. 15395 - 15401
(2007/10/03)

Tandem type polymerization. Synthesis and characterization of ordered poly(amide-thioether) from 2,6-dichlorophenyl methacrylate, 4,4′-thiobis(benznenethiol), and 4,4′-oxydianiline
Ordered poly(amide-thioether) (17) was prepared by tandem type polymerization of 2,4-dichlorophenyl acrylate (11), 4,4′-thiobis(benznenthiol) (12), and 4,4′-oxydianiline (16). The polymerization was carried out by mixing all monomers in the presence of catalytic amounts of triethylamine (TEA) and 1-hydroxybenzotriazole (HOBt) in 1-methyl-2-pyrrolidinone (NMP) at 20 °C for 2 h and then 80 °C for 2 days, yielding polymer 17 with a number-average molecular weight (Mn) of 25 000. Authentic ordered poly(amide-thioether) (18) was prepared to verify the structure of polymer 17. The microstructure of polymers obtained was investigated by 1H and 13C NMR spectroscopy, and it has been found the polymer obtained has the expected ordered structure. Furthermore, model reactions were studied in detail to demonstrate the feasibility of ordered polymer formation.
Tsuchiya, Kousuke,Shibasaki, Yuji,Ueda, Mitsuru
p. 1815 - 1818
(2007/10/03)

Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation
As a part of our project directed at the search of new chemotherapeutic agents against American trypanosomiasis (Chagas' disease), several drugs possessing the 4-phenoxyphenoxy skeleton and other closely related structures employing the thiocyanate moiety as polar end group were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the parasite responsible for this disease. These thiocyanate analogues were envisioned bearing in mind the potent activity shown by 4- phenoxyphenoxyethyl thiocyanate (compound 8) taken as lead drug. This compound had previously proved to be an extremely active growth inhibitor against T. cruzi with IC50 values ranging from the very low micromolar level in epimastigotes to the low nanomolar level in the intracellular form of the parasite. Of the designed compounds, the ethyl thiocyanate drugs connected to nonpolar skeletons, namely, arylthio, 2,4-dichlorophenoxy, ortho-substituted aryloxy, and 2-methyl-4-phenoxyphenoxy (compounds 15, 34, 47, 52, 72, respectively), were shown to be very potent antireplicative agents against T. cruzi. On the other hand, conformationally restricted analogues as well as branched derivatives at the aliphatic side chain were shown to be moderately active against T. cruzi growth. The biological activity of drugs bearing the thiocyanate group correlated quite well with the activity exhibited by their normal precursors, the tetrahydropyranyl ether derivatives, when bonded to the same nonpolar skeleton. Compounds having the tetrahydropyranyl moiety as polar end were proportionally much less active than sulfur-containing derivatives in all cases. Drugs 47 and 72 also resulted to be very active against the amastigote form of the parasite growing in myoblasts; however, they were slightly less active than the lead drug 8. On the other hand, compounds 34 and 52 were almost devoid of activity against myoblasts. Surprisingly, the dithio derivative 15 was toxic for myoblasts.
Szajnman, Sergio H.,Yan, Wen,Bailey, Brian N.,Docampo, Roberto,Elhalem, Eleonora,Rodriguez, Juan B.
p. 1826 - 1840
(2007/10/03)