cas 719-59-5, 2-Amino-5-chlorobenzophenone

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Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
supporting information
p. 12309 - 12312
(2021/12/07)

Preparation method of 2-amino-5-chlorobenzophenone
The present invention proposes a method for preparing 2-amino-5-chlorobenzophenone, comprising: Step S1, the 5-chloro-3-phenyl-2,1-benzisoxazole is mixed with a catalyst, ethyl acetate is added, stirred until dissolved, the reaction system is maintained in a hydrogen atmosphere, the reaction pressure is controlled at 1-5atm, 20-30 ° C reaction; step S2, the reaction solution obtained in step S1 is filtered and the solvent is removed, the thick is obtained, a crystalline solvent is added to the thick, and after heating and dissolving, Cooling crystallization is filtered to give 2-amino-5-chlorobenzophenone. The preparation of the opposite of the present invention compared to the prior art, the yield of the product is higher, while there are fewer impurities, the reaction conditions are relatively mild, suitable for large-scale industrial applications.
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Paragraph 0025-0053

(2022/01/08)

One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.
Fan, Hui,Xu, Shijie,Yang, Fan,Zhang, Xiaoxiang,Zhao, Xuechun
supporting information
p. 4555 - 4558
(2021/08/30)

Copper-Catalyzed Electrophilic Amination of Arylboronic Acids with Anthranils: An Access to N-Aryl-2-aminophenones
An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, and operational simplicity. Moreover, a tandem C-H borylation and C-N coupling protocol has also been developed to transform simple arenes to the valuable N-aryl-2-aminophenones in one pot. Additionally, the synthetic potential of this methodology is further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
Gao, Yang,Yang, Simin,Li, Yibiao,Huo, Yanping,Huang, Zongyi,Chen, Zumin,Hu, Xiao-Qiang
p. 10222 - 10231
(2020/09/03)

Xantphos-ligated palladium dithiolates: An unprecedented and convenient catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction with high turnover number and turnover frequency
Xantphos- and dithiolate-ligated macrocyclic palladium complexes as an efficient and stable catalyst for the carbonylative Suzuki–Miyaura cross-coupling reaction have been synthesized. The catalysts were characterized by 1H-nuclear magnetic resonance (NMR), CHNS (carbon, hydrogen, nitrogen, and sulfur) analysis, melting point analysis, and 31P-NMR spectroscopy. Several sensitive functional groups (e.g., –NO2, –F, –Cl, –Br, –NH2, and –CN) on the aromatic ring were well tolerated in the carbonylative Suzuki–Miyaura coupling reaction. The present palladium complexes produce six times higher turnover number (TON) and five times higher turnover frequency (TOF) compared with conventional homogeneous palladium precursors. Maximum TONs in the range of 105 to 106 and TOF in the range of 104 to 105 could be generated by a very low amount of catalyst loading (10–5?mol%).
Gaikwad, Vinayak V.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.
(2019/11/19)

One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
p. 2438 - 2455
(2020/01/31)

A 2 - amino -5 - chloro benzophenone (by machine translation)
The invention relates to the field of organic synthetic technology, in particular to a 2 - amino - 5 - chloro benzophenone synthetic method, its use to P-chloroaniline and benzoyl chloride in a Friedel-crafts acylation reaction for the preparation of 2 - amino - 5 - chloro benzophenone, however, the reaction can be carried out under natural conditions, anhydrous conditions without the strict requirements. Point of its technological scheme comprises a S1: chlorine increase with the benzoyl-chloroaniline will be uniformly mixed in to the reaction kettle; S2: in the reactor to continue to add catalyst iridium trioxide, mix, and keep the air flow smoothly; S3: the reaction kettle temperature stable, the normal reaction; S4: to the end of the reaction, to the reaction kettle adding nitric acid solution, stirring and mixing; S5: standing, to be system layered, removing the supernatant liquid; S6: a lower liquid refluxing reaction, and the crystallization treatment to get a product. (by machine translation)
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0069

(2019/03/28)

Method for producing 2-amino-5-chlorodiphenylketone
The invention relates to the technical field of organic synthesis, in particular to a method for producing 2-amino-5-chlorodiphenylketone. The 2-amino-5-chlorodiphenylketone is prepared by enabling p-chloroaniline and benzoyl chloride to be subjected to a Friedel-Crafts acylation reaction; however, the reaction can be carried out under the natural condition, and the anhydrous condition does not need to be strictly required. The method is characterized by comprising the following steps: S1, adding the p-chloroaniline and the benzoyl chloride into a reaction kettle and mixing uniformly; S2, continuing to add a catalyst dysprosium trioxide into the reaction kettle, mixing uniformly, and keeping air flowing; S3, controlling the temperature in the reaction kettle to be stable, enabling the reaction to be carried out normally; S4, after the reaction is completed, adding a nitric acid solution into the reaction kettle, and evenly mixing; S5, standing until the system is layered, and then removing supernatant liquid; S6, enabling underlayer liquid to be subjected to a reflux reaction, and carrying out crystallization treatment to obtain the product.
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Paragraph 0027-0068

(2019/03/28)

Preparation method of 2-amino-5-chlorobenzophenone
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-amino-5-chlorobenzophenone. The method prepares the 2-amino-5-chlorobenzophenone through Friedel-Crafts acylation between parachloroaniline and benzoyl chloride, however, the Friedel-Crafts acylation can be performed in natural conditions and does not need to strictly require anhydrous conditions. The technical scheme comprises the following points: S1, feeding parachloroaniline and benzoyl chloride into a reaction kettle and uniformly mixing; S2, continuously feeding catalyst dysprosium oxide into the reaction kettle, uniformly mixing, and keeping an air flow unobstructed; S3, controlling temperature in the reaction kettle to be stale, so as to ensure that reaction is normally operated; S4, feeding a hydrochloric acid solution into the reaction kettle after the reaction is finished, and uniformly stirring and mixing; S5, leaving the solution to stand, and removing liquid in the upper layer after a system is layered; S6, ensuring that liquid in the lower layer is subjected to reflux reaction, and performing crystallization treatment, so as to obtain a product.
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Paragraph 0026-0061; 0067-0068

(2019/02/26)

Industrial production method for preparing 2-amino-5-chlorobenzophenone
The invention relates to the technical field of organic synthesis, and especially relates to an industrial production method for preparing 2-amino-5-chlorobenzophenone. The 2-amino-5-chlorobenzophenone is prepared by a Friedel-Crafts acylation reaction of p-chloroaniline and benzoyl chloride, and the reaction is carried out under natural conditions without the strict requirement of anhydrous conditions. The method includes the following steps: S1, adding the p-chloroaniline and benzoyl chloride into a reaction kettle, and performing uniform mixing; S2, continuously adding a catalyst yttria into the reaction kettle, performing uniform mixing, and keeping air flowing smoothly; S3, controlling the temperature in the reaction kettle to be stable in order to make the reaction carried out normally; S4, adding a hydrochloric acid solution into the reaction kettle after the reaction is completed, and performing stirring for uniform mixing; S5, standing the obtained system to layer the system,and removing the obtained upper liquid; and S6, carrying out a refluxing reaction on the above obtained lower liquid, and carrying out crystallization treatment to obtain the product.
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Paragraph 0022-0068

(2019/02/13)

Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information
p. 12724 - 12729
(2019/11/05)

Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.
Li, Quanzhe,Yu, Liuzhu,Wei, Yin,Shi, Min
p. 9282 - 9296
(2019/08/12)

Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source
A palladium-catalyzed reductive and carbonylative cyclization of ortho-iodo-tethered methylenecyclopropanes (MCPs) using N-formylsaccharin as CO source has been developed, affording the desired indanone derivatives in moderate to good yields with high regio- and stereoselectivity and good functional group compatibility.
Fan, Xing,Shi, Min,Wei, Yin
p. 5677 - 5683
(2019/11/16)

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
supporting information
p. 3085 - 3090
(2019/08/07)

Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement
A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.
Fan, Xing,Wang, Qiang,Wei, Yin,Shi, Min
p. 10503 - 10506
(2018/09/21)

Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.
Li, Peng-Hua,Yu, Liu-Zhu,Zhang, Xiao-Yu,Shi, Min
p. 4516 - 4520
(2018/08/09)

Preparation method of alprazolam intermediate
The invention discloses a preparation method of an alprazolam intermediate. The method comprises the following steps: sequentially adding methanol and p-nitrochlorobenzene in a sodium hydroxide watersolution, dropwise adding phenylacetonitrile under stirring, reacting at 40 +/-5 DEG C after the dropwise addition is finished, and carrying out post-treatment to obtain an intermediate (II) ; and dissolving the intermediate (II) in ethanol, adding iron powder, refluxing, dropwise adding sulfuric acid, refluxing for 1 hour, and carrying out post-treatment to obtain an intermediate(III). Accordingto the method disclosed by the invention, the sodium hydroxide water solution is used in the synthesis of the intermediate (II) to replace a dangerous mode of refluxing and dissolving solid sodium hydroxide by using ethanol, a small amount of methanol is added into the reaction system, and the problem of two-phase reaction is successfully solved. The sulfuric acid is used for replacing volatile hydrochloric acid during the synthesis of the intermediate (III), the reaction time is effectively shortened, and the reaction efficiency is improved. The method disclosed by the invention is safer to operate, short in reaction time and more suitable for industrial production.
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Paragraph 0032; 0034; 0040

(2018/07/30)

Method for synthesizing 2-amino-5-chlorobenzophenone by microchannel reactor
The invention discloses a method for synthesizing 2-amino-5-chlorobenzophenone by a microchannel reactor, belongs to the field of synthesis of psychoactive drugs in organic synthesis, and solves the problems of low yield, poor purity, high risk of violent explosion, degradation caused by high reaction time under high temperature and high pressure conditions, low frequency of catalyst recycling andreuse and the like during the synthesis of a traditional catalytic hydrogenation reactor. The method for synthesizing the 2-amino-5-chlorobenzophenone in the microchannel reactor specifically includes the following steps: 1). adding hydrogenation reaction precursor 5-chloro-3-phenyl-2,1-benzisoxazole into an organic solvent, and then adding an activated-carbon-loaded noble metal catalyst to obtain a mixture as a material I to enter a preheating module of the microreactor; and 2). after preheating of the material I, injecting the material I and material II hydrogen into a reaction module groupof the microreactor for reaction, collecting a reaction solution flowing out from a cooling module, and treating to obtain the 2-amino-5-chlorobenzophenone. The method is suitable for the large-scaleproduction of the 2-amino-5-chlorobenzophenone.
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Paragraph 0034-0063; 0067-0074

(2018/06/15)

Preparation method of 2-amino-5- chlorobenzophenone
The invention discloses a preparation method of 2-amino-5- chlorobenzophenone. The preparation method comprises the following steps: (1) mixing ethanol with the mass concentration of 95%, sodium hydroxide, parachloronitrobenzene and benzyl cyanide, mixing the mixture and performing ultrasonic oscillation on the mixture at the temperature of 25-35 DEG C for 1h; (2) performing microwave heating on aproduct obtained in step (1) for 10min, adding water in a system, filtering, washing filter residues with methanol three times and drying the filter residues, so as to obtain 5-chlorine-3-phenyl-2, 1-benzisoxazole; (3) mixing methanol, the 5-chlorine-3-phenyl-2, 1-benzisoxazole, a palladium carbon catalyst and ammonium formate, heating and refluxing for 2h, cooling to room temperature, filteringand performing vacuum drying on the filter residues. The method provided by the invention is high in product yield, short in reaction time and less in waste discharge and is environmentally friendly.
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Paragraph 0014; 0015; 0016; 0017

(2018/03/26)

Preparation method of 2-amino-5-chlorobenzophenone
The invention discloses a preparation method of 2-amino-5-chlorobenzophenone. The preparation method of 2-amino-5-chlorobenzophenone comprises the following steps: (1) mixing ethanol and sodium hydroxide, performing heating reflux, adding parachloronitrobenzene, stirring for 30 to 60 minutes, cooling to 28 DEG C, adding benzyl cyanide, reacting at 25 to 35 DEG C for 3 hours and naturally cooling to room temperature; (2) performing microwave heating, adding water, filtering, washing the filter residue with methanol and drying to obtain 5-chlorine-3-phenyl-2,1 benzisoxazole; and (3) performing heating reflux on 5-chlorine-3-phenyl-2,1 benzisoxazole, iron powder and ethanol, dropwise adding a hydrochloric acid ethanol solution into a system, refluxing at 35 DEG C for 2 hours, adjusting the pHof the system to be 7 to 8, adding activated carbon into the system, continuously refluxing, filtering and vacuum-drying the filter residue to obtain 2-amino-5-chlorobenzophenone. By the method, theyield of products is high and can reach to 94 percent, the reaction time is short, emission of waste is reduced, and the production method is environment-friendly.
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Paragraph 0014; 0015; 0016

(2018/03/26)

Synthesis method of 2-amino-5-chlorobenzophenone
The invention discloses a synthesis method of 2-amino-5-chlorobenzophenone. The method comprises the following steps: (1) mixing ethanol having a mass concentration of 95% with sodium hydroxide, parachloronitrobenzene and phenylacetonitrile, stirring, and carrying out ultrasonic oscillating at the temperature of 25-35 DEG C; (2) carrying out microwave heating, adding water into a system, filtering, washing filter residue with methanol, and then drying to obtain 5-chloro-3-phenyl-2,1-benzisoxazole; (3) mixing tetrahydrofuran with triethylamine, then adding the 5-chloro-3-phenyl-2,1-benzisoxazole and a palladium carbon catalyst and mixing, introducing nitrogen, carrying out air replacement, then introducing nitrogen until the pressure is 0.1MPa, and carrying out magnetic stirring; then, filtering, and carrying out vacuum drying on the obtained filter residue so as to obtain the 2-amino-5-chlorobenzophenone. The method provided by the invention has the advantages that product yield is high, and can reach 95%; the reaction time is short, waste emission is reduced, and the production method is environmentally-friendly.
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Paragraph 0014; 0015; 0016

(2018/07/30)

Chemoselective double annulation of two different isocyanides: Rapid access to trifluoromethylated indole-fused heterocycles
An unprecedented chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-α]indoles in a single operation from readily available starting materials. Isocyanide insertion into C=O double bonds is disclosed for the first time as indicated by the results of 18O-labeling experiment. A mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides, followed by indole-2,3-epoxide formation and rearrangement.
Gao, Yuelei,Hu, Zhongyan,Dong, Jinhuan,Liu, Jun,Xu, Xianxiu
supporting information
p. 5292 - 5295
(2017/11/06)

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles
An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.
Fan, Xing,Yu, Liu-Zhu,Wei, Yin,Shi, Min
p. 4476 - 4479
(2017/09/11)

Synthetic method of Oxazolam drug intermediate 2-amino-5-chlorobenzophenone
A synthetic method of an Oxazolam drug intermediate 2-amino-5-chlorobenzophenone comprises the following steps: adding 3.51-3.55mol of benzamide into a reaction container provided with a stirrer, a thermometer and a reflux condenser, rising the temperature of a solution to 120-123 DEG C, dropwise adding 1.41mol of p-chloroaniline, after adding, slowly rising the temperature to 190-195 DEG C, adding 5.5-5.9 mol of stannous chloride, rising the temperature of a solution to 240-250 DEG C, reacting for 3-4h at the temperature until no gas is generated, reducing the temperature of a solution to 90-95 DEG C, adding 500ml of a potassium chloride solution, rising the temperature of a solution to 130 DEG C, performing backflow, pouring out a water layer after 3-4h, cooling a solution, then separating out a dark suspended matter, adding the suspended matter into 2.5L of a phosphoric acid solution, performing backflow for 20-23h, cooling, then pouring a solution into 1200ml of a sodium nitrate solution, reducing the temperature of a solution to 5-8 DEG C, adding cyclohexane for extraction, adding 300ml of a sodium sulfite solution in a cyclohexane layer, performing reduced pressure distillation, adding acetonitrile and extracting for 5-7 times, separating out a solid, filtering, and dehydrating by a dehydrating agent, thus obtaining the yellow crystal 2-amino-5-chlorobenzophenone.
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Paragraph 0016; 0017

(2017/03/08)

2-Arylindoles: A new entry to transition metal-free synthesis of 2-aminobenzophenones
Various 2-aminobenzophenones were synthesized from readily available 2-arylindoles in DMSO under O2 balloon atmosphere. The synthesis was carried out without the aid of a transition metal catalyst or moisture-sensitive organometallic reagents from 2-arylindoles.
Yu, Jin,Moon, Hye Ran,Min, Beom Kyu,Kim, Jae Nyoung
supporting information
p. 893 - 897
(2016/06/14)

Synthetic method for diazepamum drug intermediate 2-amino-5-chloro-benzophenone
The invention discloses a synthetic method for a diazepamum drug intermediate 2-amino-5-chloro-benzophenone. The synthetic method comprises the following steps: subjecting 5-chloro-3-phenyl-benzisoxazole (as shown in a formula 2) and nickel chloride powder to a heating reflux reaction in a 2-bromo-5-fluoronitrobenzene solution; then adding a 4-(chlorophenyl)ethylamine solution and a glycol dimethyl ether solution and continuing the reflux reaction; and adding a sodium bicarbonate solution, carrying out cooling, decoloring, filtering, filtrate concentration, cooling again, washing and dehydration so as to obtain the crystal 2-amino-5-chloro-benzophenone. Compared with synthetic methods in the prior art, the synthetic method provided by the invention is greatly shortened in reaction time; and the synthetic method provides a novel synthetic route and lays good foundation for further improvement of reaction yield.
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Paragraph 0021-0025

(2017/07/21)

Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
Chen, Jiuxi,Ye, Leping,Su, Weike
supporting information
p. 8204 - 8211
(2015/01/08)

Palladium-catalyzed direct addition of 2-Aminobenzonitriles to sodium arylsulfinates: Synthesis of o-Aminobenzophenones
The first example of the palladium-catalyzed synthesis of o-Aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-Aminobenzonitriles was reported. A plausible mechanism for the formation of o-Aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-Aminobenzophenones.
Chen, Jiuxi,Li, Jianjun,Su, Weike
p. 6439 - 6449
(2014/06/10)

Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent
A series of novel substituted aminobenzophenone derivatives containing nitrogen mustard moiety (5a-f) were synthesized and characterized on the basis of their IR, 1H NMR, 13C NMR, CHN, and mass spectral data. All the compounds when evaluated for chemical 4-(4-nitrobenzyl) pyridine alkylating activity proved to be active alkylating agents. All the synthesized compounds were subjected to physicochemical parameters determination required for central nervous system (CNS) activity through computational, online software, and QikProp 3.2. The log P values and other in silico ADME physicochemical descriptors analyzed lay between the ranges those are required for good BBB penetration. The in vitro antiproliferative activity against human cancer cell lines viz. A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) was investigated. Most of the test compounds showed potent antitumor activity, especially compound (5f) which displayed the highest activity against CNS cancer cell line comparable to that of chlorambucil and docetaxel. The preliminary structure-activity relationship (SAR) revealed that 5-chloroaminobenzophenone-mustard series (5a-c) exhibited better antitumor activity than 5-nitroaminobenzophenone-mustard series (5d-f).
Singh, Rajesh K.,Prasad,Bhardwaj
p. 5901 - 5911
(2013/11/06)

Synthesis of 2-aminobenzophenone derivatives and their anticancer activity
A number of 2-aminobenzophenones have been synthesized by acylation of para-chloroaniline with different 2-, 3-, 4-chloro-or fluorobenzoyl chloride in solid state via the Friedel-Crafts reaction. Synthesized compounds were characterized by 1H and 13C NMR, Fourier transform-infrared, ultraviolet-visible spectroscopy, mass spectrometry, and elemental analysis. Evaluation of biological activity in vitro showed that the selected compounds 9, 10, and 13 have potential anticancer activity. The presence of one chlorine atom in the second aromatic ring of the benzophenone molecule makes it more active.
Cortez-Maya,Cortes Cortes,Hernandez-Ortega,Apan, T. Ramirez,Martinez-Garcia
experimental part
p. 46 - 54
(2011/10/31)

Development and a practical synthesis of nepafenac intermediate via modified gassman reaction
Modification of nepafenac intermediate synthesis (5A) via Gassman specific ortho-substitution is reported. According to the process, 2-aminobenzophenone (1A) and 2-(methylthio)acetamide (2) were reacted in the convenient temperature conditions, in the presence of N-chlorophthalimide (3) or 1,3-dichloro-5,5- dimethylhydantoin (4), to activate the formation of azasulfonium salt and rearrangement thereof to pure 2-amino-3-benzoyl-α-(methylthio) phenylacetamide (5A). The procedure appears to be suitable for a reaction carried out in a large scale.
Cybulski, Marcin,Formela, Adam,Mucha, Mariola,Klos, Karolina,Roszczynski, Jacek,Winiarski, Jerzy
p. 461 - 464,4
(2020/08/24)

Synthesis of quinolin-2-one alkaloid derivatives and their inhibitory activities against HIV-1 reverse transcriptase
Based on an established common pharmacophore of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNTTIs), a series of quinolin-2-one derivatives were synthesized and assayed for their in vitro activities against HIV-1 reverse transcriptase (RT) for the first time. Some of the tested compounds were active against HIV-1 RT. Compounds 4a2 and 4d2 showed inhibitory activities with IC50 values of 0.21 and 0.15 μM, respectively, with a mode of interaction with RT residues of the allosteric pocket similar to that of efavirenz.
Cheng, Pi,Gu, Qiong,Liu, Wei,Zou, Jian-Feng,Ou, Yang-Yong,Luo, Zhong-Yong,Zeng, Jian-Guo
p. 7649 - 7661
(2011/11/05)

Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
Yan, Yizhe,Wang, Zhiyong
p. 9513 - 9515
(2011/10/01)

A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
supporting information; experimental part
p. 2841 - 2843
(2010/09/04)

A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
supporting information; experimental part
p. 5244 - 5246
(2010/09/05)

Discovery of novel benzoxazinones as potent and orally active long chain fatty acid elongase 6 inhibitors
A series of benzoxazinones was synthesized and evaluated as novel long chain fatty acid elongase 6 (ELOVL6) inhibitors. Exploration of the SAR of the UHTS lead 1a led to the identification of (S)-1y that possesses a unique chiral quarternary center and a
Mizutani, Takashi,Ishikawa, Shiho,Nagase, Tsuyoshi,Takahashi, Hidekazu,Fujimura, Takashi,Sasaki, Takahide,Nagumo, Akira,Shimamura, Ken,Miyamoto, Yasuhisa,Kitazawa, Hidefumi,Kanesaka, Maki,Yoshimoto, Ryo,Aragane, Katsumi,Tokita, Shigeru,Sato, Nagaaki
supporting information; experimental part
p. 7289 - 7300
(2010/06/16)

Process For Preparing A Benzoylbenzeneacetamide Derivative
Disclosed is a process for preparing anti-inflammatory compound nepafenac comprising preparing a compound of formula (V) wherein a N-halosuccinimide is used as the halogenating agent, followed by desulfurization using Raney Nickel. Also disclosed is a polymorphic form B of 2-amino-3-benzoyl-α-(methylthio)-benzeneacetamide (i.e., a compound of formula (V) wherein R is methyl
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(2009/12/27)

An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex
An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.
Mannam, Sreedevi,Sekar, Govindasamy
experimental part
p. 497 - 502
(2009/07/18)

Bakers' yeast-catalyzed reductive cleavage of 3-aryl-2,1-benzisoxazoles and its quaternary salts: An efficient green synthesis of 2-aminobenzophenones
3-Aryl-2,1-benzisoxazoles and its salts underwent reductive cleavage of the N-O bond leading to 2-aminobenzophenones with bakers' yeast under non-fermenting conditions in aqueous media. The procedure gives excellent yields of 2-alkylamino- and 2-aminobenzophenones.
Lekhok, Kushal C.,Prajapati, Dipak,Boruah, Ramesh C.,Mazumder, Sharbani,Borah, Tarun C.
experimental part
p. 1183 - 1187
(2011/10/01)

Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives
A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).
Cheng, Pi,Zhang, Quan,Ma, Yun-Bao,Jiang, Zhi-Yong,Zhang, Xue-Mei,Zhang, Feng-Xue,Chen, Ji-Jun
supporting information; experimental part
p. 3787 - 3789
(2009/04/06)

Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by a DABCO-copper complex under mild conditions
A DABCO-copper(I) chloride complex (5 mol%) together with TEMPO (5 mol%) in nitromethane as solvent has been used as an efficient catalytic system for the selective oxidation of benzylic and allylic alcohols into the corresponding carbonyl compounds at room temperature where molecular oxygen acts as an ultimate, stoichiometric oxidant and water is the only by-product. The solidstate structure determination of the DABCOcopper complex shows that the copper is in the + II oxidation state with trigonal bipyramidal geometry and exists in a linear polymeric structure due to strong hydrogen bonding.
Mannam, Sreedevi,Alamsetti, S. Kumar,Sekar
p. 2253 - 2258
(2008/09/18)

Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction
A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus.
Butin, Alexander V.,Smirnov, Sergey K.,Stroganova, Tatyana A.,Bender, Wolfgang,Krapivin, Gennady D.
p. 474 - 491
(2007/10/03)

Kinetic and mechanistic studies on the hydrolysis and photodegradation of diazepam and alprazolam
The corresponding o-aminobenzophenones are usually reported as the main degradation products in the hydrolysis of 1,4-benzodiazepinones. Nevertheless, in previous studies of diazepam (DZ) in acidic aqueous medium we isolated and characterized seven unexpected degradation products. Kinetic measurements under several reaction conditions shed some light on the mechanisms of the complex reactions that are taking place, and photochemical studies give hints on the mechanisms of chlorination and annelation processes. Alprazolam (AL) seems to exhibit an unusually high stability against hydrolysis under several conditions; nevertheless, the structure is sensitive to photolytic cleavage. The photodegradation of AL was studied in aqueous and methanolic solutions. Characterization of the isolated products by 1H and 13C NMR and mass spectrometry revealed that electron transfer, oxidation and rearrangement reactions take place. The influence of several variables such as pH, solvent composition and light irradiation were examined and mechanisms for the formation of three photoproducts are proposed. A specific method for the determination of AL in the presence of photoproducts was developed, which allowed kinetic determinations of the photostability of AL. The photosensitivity observed in some patients treated with AL seems to be due to one of the characterized photoproducts. Copyright
Cabrera, C. Gallardo,Goldberg De Waisbaum,Nudelman, N. Sbarbati
p. 156 - 161
(2007/10/03)

Preparation of 2-arninpbenzophenones and polysubstituted quinolines through Sml2 promoted reductive cleavage of 3-aryl-2,1-benzisoxazoles
Promoted by SmI2, 3-aryl-2,1-benzisoxazoles underwent reductive cleavage of the N - O bond leading to 2-aminobenzophenones in high yields upon protonation. Otherwise, if ketones with active methylene group were added to the reaction mixture prior to protonation, the desired poly substituted quinolines could be obtained under mild conditions in a one-pot manner.
Fan, Xuesen,Zhang, Xinying,Zhang, Yongmin
p. 637 - 643
(2007/10/03)

Potential plant growth regulators: Synthesis and activity of new substituted N-(2-benzoyl-4-chlorophenyl)benzamides and N-[4-chloro-2-(α, α-hydroxyphenylmethyl)phenyl]benzamides
2-Amino-5-chlorobenzophenone 3 prepared in 2 steps from isatoic anhydride 1 on condensation with substituted benzoyl chlorides 6a-i in presence of Et 3N in 1,2-dichloroethane (DCE) affords substituted N-(2-benzoyl-4-chlorophenyl)-benzamides 7a-i which on reduction with NaBH 4 gives corresponding alcohols, N-[4-chloro-2-(α,α- hydroxyphenyl-methyl)phenyl]benzamides 8a-i. The structures of all the compounds are confirmed by 1H NMR spectra, and their cytokinin (plant growth promoting) activity is determined on seeds of Raphanus sativus, family Brassicaceae (common name white radish, variety Pusa Chetki), for concentrations varying between 0.1 to 10 mg/litre. Compounds 7c, 7d, 7g and 7h at all concentrations and 7i at 4 concentrations have been found to show higher plant growth promoting (PGP) activity than benzyladenine (standard). Compounds 8d and 8g also show moderate plant growth promoting (cytokinin) activity, while compounds 7a, 7b, 7e, 7f and 8a, 8b, 8c, 8e, 8f and 8i are found to have plant growth inhibiting (PGI) activity.
Hatim, Jaywant Govind,Joshi, Vidya
p. 2689 - 2695
(2007/10/03)

Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof
The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).
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(2010/02/06)

Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors
A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-1enzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo.
Hu, Wenhui,Guo, Zongru,Chu, Fengming,Bai, Aiping,Yi, Xiang,Cheng, Guifang,Li, Jing
p. 1153 - 1160
(2007/10/03)

Synthesis of all stereoisomers and some congeners of isocytoxazone
cis-Isocytoxazone 2a and trans-isocytoxazone 2b, structural isomers of the antiasthmatic agent cytoxazone (-)-1, and their 5-substituted congeners 23-28 have been prepared. Aldol reaction of para-substituted benzaldehydes with 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one, followed by separation of diastereomeric racemates afforded 3-10. Acid-catalyzed 1,4-benzodiazepine ring opening, and transformation of the methyl esters of β-aryl-β-hydroxy-α-amino acids (11-16) via 4-methoxycarbonyl derivatives of 1,3-oxazolidin-2-one (17-22) and their reduction afforded the target oxazolidin-2-one derivatives 23-28. Racemic isocytoxazones 2a and 2b were prepared by an independent route starting from 4-methoxystyrene epoxide. Pure enantiomers of these diastereomeric racemates were separated by HPLC chromatography on chiral stationary phases. Their CD spectra, along with those of previously prepared enantiomers of cis-cytoxazone 1a and trans-cytoxazone 1b are discussed.
Hamer?ak, Zdenko,?epac, Dragan,?iher, Dinko,?unji?, Vitomir
p. 375 - 382
(2007/10/03)

Water promoted iodotrimethyl silane reactions: Reductive cleavage of isoxazolidines and 2,1-benzisoxazoles to γ-amino alcohols and o-aminobenzophenones
Water promoted iodotrimethyl silane [ITMS] reductively cleaved isoxazolidines and 2,1-benzisoxazoles to γ-amino alcohols and o-aminobenzophenones respectively at shorter times and in higher yields at room temperature.
Boruah, Monalisa,Konwar, Dilip
p. 601 - 603
(2007/10/03)

SmI2-mediated facile one-pot preparation of 2,4-diarylquinolines from 3-aryl-2,1-benzisoxazoles
On treatment with SmI2, 3-aryl-2,1-benzisoxazoles undergo reductive cleavage of the N-O bond leading to 2-aminobenzophenones in high yields upon protonation. If aryl methyl ketones are added to the reaction mixture prior to protonation, the desired 2,4-diarylquinolines can be obtained in moderate yields under mild conditions.
Fan, Xuesen,Zhang, Yongmin
p. 7001 - 7003
(2007/10/03)