cas 99-73-0, 2,4'-Dibromoacetophenone | Articles data

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IMIDAZOTHIAZOLE COMPOUNDS AND METHODS FOR TREATING PLANT NEMATODE INFECTIONS
The present application relates to the treatment of nematode infections in a plant. For example, the application relates to the use of one or more compounds of Formula (I) as defined herein, or compositions comprising these compounds, for treatment of a nematode infection or a disease, disorder or condition arising from a nematode infection in a plant. (Formula I)
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Paragraph 00118-00119

(2021/01/29)

Thiazole ring-containing amide compounds as well as preparation method and application thereof
The invention discloses thiazole ring-containing amide compounds as well as a preparation method and application thereof, and belongs to the field of chemical technologies and pesticides. According to the present invention, p-phenylenediamine is adopted as a raw material to synthesize a series of the thiazole ring-containing amide compounds, and the synthesized thiazole ring-containing amide compounds have good inhibition effects on Xanthomonas oryzae pv.Oryza (Xoo), Xanthomonas oryzae pv.Oryzcola (Xoc) and Xanthomonas axonophora pv.Citri (Xac) in agricultural diseases and insect pests, and can be used for preparing the anti-plant bacterium agent.
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Paragraph 0044; 0051; 0078; 0081; 0150; 0155; 0234; 0239

(2021/06/23)

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
supporting information
p. 429 - 432
(2020/02/29)

Synthesis of novel quaternary ammonium salts from 1, 2-benzothiazine derivatives
A series of novel 1,2-benzothiazine based quaternary ammonium salts were successfully prepared through different organic transformations. Products of all transformations and final salts were separated out and purified. The product yields were good to exce
Gul, Salman,Saleem, Maria,Munawar, Munawar Ali,Ahmad, Hafiz Adnan,Ahmed, Ejaz,Begum, Robina,Farooqi, Zahoor H.
p. 15 - 28
(2020/08/05)

1,3-Diarylpyrazolyl-acylsulfonamides as Potent Anti-tuberculosis Agents Targeting Cell Wall Biosynthesis in Mycobacterium tuberculosis
Phenotypic whole cell high-throughput screening of a μ150,000 diverse set of compounds against Mycobacterium tuberculosis (Mtb) in cholesterol-containing media identified 1,3-diarylpyrazolyl-acylsulfonamide 1 as a moderately active hit. Structure-activity
Abay, Efrem,Barry, Clifton E.,Basarab, Gregory S.,Boshoff, Helena I. M.,Boyle, Grant A.,Chibale, Kelly,Eyermann, Charles J.,Fienberg, Stephen,Ghorpade, Sandeep R.,Khonde, Lutete Peguy,Lawrence, Nina,Lenaerts, Anne J.,Massoudi, Lisa M.,Myers, Timothy G.,Myrick, Alissa,Nchinda, Aloysius T.,Njoroge, Mathew,Reddy, Virsinha,Robertson, Gregory T.,Singh, Vinayak,Sirgel, Frederick A.,Su, Qin,Van Helden, Paul D.,Müller, Rudolf
supporting information
p. 12790 - 12807
(2021/09/11)

Structure-activity relationship studies for the development of inhibitors of murine adipose triglyceride lipase (ATGL)
High serum fatty acid (FA) levels are causally linked to the development of insulin resistance, which eventually progresses to type 2 diabetes and non-alcoholic fatty liver disease (NAFLD) generalized in the term metabolic syndrome. Adipose triglyceride lipase (ATGL) is the initial enzyme in the hydrolysis of intracellular triacylglycerol (TG) stores, liberating fatty acids that are released from adipocytes into the circulation. Hence, ATGL-specific inhibitors have the potential to lower circulating FA concentrations, and counteract the development of insulin resistance and NAFLD. In this article, we report about structure–activity relationship (SAR) studies of small molecule inhibitors of murine ATGL which led to the development of Atglistatin. Atglistatin is a specific inhibitor of murine ATGL, which has proven useful for the validation of ATGL as a potential drug target.
Breinbauer, Rolf,Doler, Carina,Fuchs, Elisabeth,Grabner, Gernot F.,Mayer, Nicole,Melcher, Michaela-Christina,Migglautsch, Anna K.,Romauch, Matthias,Schweiger, Martina,Zechner, Rudolf,Zimmermann, Robert
supporting information

(2020/07/13)

Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System
A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.
Cheng, Zhao,Guo, Hongmei,Huang, Guozheng,Rexit, Abulikemu Abudu,Wang, Hui,Zheng, Meng-Xia
p. 6455 - 6458
(2020/10/21)

Synthesis, inhibition studies against AChE and BChE, drug-like profiling, kinetic analysis and molecular docking studies of N-(4-phenyl-3-aroyl-2(3H)-ylidene) substituted acetamides
Halogenated and non-halogenated N-(4-phenyl-3-aroyl-2(3H)-ylidene) substituted acetamides were prepared by base-catalyzed cyclization of corresponding acetyl thioureas with phenacyl bromide. The synthesized compounds were structurally characterized by 1H NMR and 13C NMR spectroscopy and were screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzyme inhibition activities. Molecular docking studies, drug-like profiling and kinetic analysis were performed to further investigate the inhibition mechanism of the compounds. This study provided useful insights into the design and development of novel dual inhibitors, in addition to understanding the mechanism by which such drugs interact with targets and exert their biochemical action. All the compounds showed superior inhibition profile compared to the standards possessing sub-micromolar and micromolar IC50 values for AChE and BChE, respectively. Docking simulations revealed that the compound 6g showed strong binding inside the active site gorges of both AChE and BChE. An excellent agreement was obtained as the best docked poses showed important binding features mostly based on interactions due to aromatic moieties and oxygen atoms of the compound. Cation-pi/pi-pi interactions together with hydrogen bond forces were the key players responsible for ligand anchoring in the active sites. The striking results accomplished both in docking computations and experimental findings ascertained that the compound 6g can serve as a scaffold for both AChE and BChE inhibition.
Larik, Fayaz Ali,Saeed, Aamer,Faisal, Muhammad,Hamdani, Salma,Jabeen, Farukh,Channar, Pervaiz Ali,Mumtaz, Amara,Khan, Imtiaz,Kazi, Mahar Ali,Abbas, Qamar,Hassan, Mubashir,Korabecny, Jan,Seo, Sung-Yum
(2019/12/09)

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.
Luo, Zhibin,Meng, Yunge,Gong, Xinchi,Wu, Jie,Zhang, Yulan,Ye, Long-Wu,Zhu, Chunyin
supporting information
p. 173 - 177
(2020/01/02)

One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid
A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol involves three reactions in one process: a tandem (formation of phenacyl bromides from styrenes) followed by a telescoped (conversion to thiazole) reaction.
de Andrade, Vitor S.C.,de Mattos, Marcio C.S.
supporting information

(2020/07/03)

Utility of N -Bromosuccinimide-Water Combination as a Green Reagent for Synthesis of N,S-Heterocycles and Dithiocarbamates from Styrenes
An efficient and unprecedented green protocol has been developed for the synthesis of N,S-heterocycles from styrenes and alkyl dithiocarbamates with high to excellent yields. The reaction of primary or secondary amines, CS 2, and styrenes was carried out in water in the presence of a catalytic amount of an inorganic base. All products were made by using an N -bromosuccinimide-H 2O combination as a green and inexpensive reagent.
Matloubi Moghaddam, Firouz,Goudarzi, Mehri
supporting information
p. 1823 - 1827
(2020/10/02)

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives
In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.
Rodríguez, Juan C.,Maldonado, Rony A.,Ramírez-García, Gonzalo,Díaz Cervantes, Erik,de la Cruz, Fabiola N.
p. 2279 - 2287
(2020/03/16)

NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates
An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility.
Muneeswara, Madithedu,Sundaravelu, Nallappan,Sekar, Govindasamy
supporting information
p. 3479 - 3484
(2019/05/21)

Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold
Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.
Nguyen, T. Vu,Minrovic, Bradley M.,Melander, Roberta J.,Melander, Christian
p. 927 - 937
(2019/03/26)

DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE
Provided herein are a dihydropyrimidine compound and a pharmaceutical application thereof, especially the application used for treating and preventing HBV diseases. Specifically, provided herein is a compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicine, especially for treating and preventing HBV diseases.
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Paragraph 00450

(2019/01/17)

Method of utilizing micro channel reactor to prepare pentafluorophenoxyl ketones continuously
The invention discloses a method of utilizing a micro channel reactor to prepare pentafluorophenoxyl ketones continuously. Cheap and easily available styrene and pentafluorophenol are taken as the primary raw materials, two step continuous reactions are carried out in a micro channel reactor to obtain pentafluorophenoxyl ketones, the reaction time is shortened to several minutes from several hours; the product yield is high, the reaction efficiency is obviously enhanced, no any pricy organic catalyst or metal catalyst is needed, the operation is simple, the cost is low, the preparation technology is easy to control, the safety is high, the reaction conditions are mild, and the method can be applied to industrial production.
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Paragraph 0046-0047

(2019/06/30)

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.
Shibasaki, Kaho,Togo, Hideo
p. 2520 - 2527
(2019/04/04)

Application of poly(vinylphenyltrimethylammonium tribromide) resin as an efficient polymeric brominating agent in the α-bromination and α-bromoacetalization of acetophenones
The applications of a new supported tribromide reagent based on poly(vinylbenzyltrimethylammonium hydroxide) resin (Amberlite 717) were reported. This supported tribromide resin was used directly in α-bromination and α-bromoacetalization of acetophenones without any other catalyst under mild conditions. The effects of solvents and the amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of α-bromo and α-bromoacetal of acetophenones were selectively obtained in excellent yields.
Han, Bingbing,Zheng, Zubiao,Zheng, Dongcheng,Zhang, Lei,Cui, Peng,Shi, Jianjun,Li, Changjiang
supporting information
p. 2512 - 2520
(2019/07/04)

Novel pyrrolo[2,3-d]pyrimidine derivatives: Design, synthesis, structure elucidation and in vitro anti-BVDV activity
The progression of drug resistance of viral infection justifies the discovering of new anti-viral agents. Thus, a novel series of pyrrolopyrimidine derivatives 5–7 and 9–18 were designed, synthesized and fully characterized by IR, mass spectroscopy, NMR,
Sroor, Farid M.,Basyouni, Wahid M.,Tohamy, Wael M.,Abdelhafez, Tawfeek H.,El-awady, Mostafa K.
(2019/11/11)

Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).
Ushakov, Pavel Yu.,Khatuntseva, Elizaveta A.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.,Sukhorukov, Alexey Yu.
supporting information
p. 5322 - 5327
(2019/11/13)

Dihydropyrimidine compound and uses of dihydropyrimidine compound in drugs
The present invention relates to a dihydropyrimidine compound and uses of the dihydropyrimidine compound as drugs, particularly as drugs for treatment and prevention of hepatitis B, particularly to acompound represented by a general formula (I) or (Ia) or an enantiomer, a diastereomer, a tautomer, a hydrate, a solvate or a pharmaceutically acceptable salt thereof, wherein each variable is definedin the specification. The invention further relates to uses of the compound represented by a general formula (I) or (Ia) or the enantiomer, the diastereomer, the tautomer, the hydrate, the solvate orthe pharmaceutically acceptable salt thereof as drugs, especially as drugs for treatment and prevention of hepatitis B. The formulas (I) and (Ia) are defined in the specification.
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Paragraph 1213; 1214; 1215; 1216

(2019/01/16)

Monoglycosyl-containing heterocyclic compound for inhibiting hepatitis C viruses and preparation method
The invention discloses a monoglycosyl-containing heterocyclic compound for inhibiting hepatitis C viruses and a preparation method. The monoglycosyl-containing heterocyclic compound has a chemical structure represented by a formula I shown in the description. The monoglycosyl-containing heterocyclic compound disclosed by the invention can be used for effectively inhibiting protease of the hepatitis C viruses and treating infection of the hepatitis C viruses (HCV).
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Paragraph 0084; 0085

(2019/03/28)

Amino propylene glycol derivatives, its preparation method and its pharmaceutical composition and use thereof
The invention discloses a class of amino propanediol derivatives, a preparation method, drug compositions and uses thereof, and particularly relates to a class of new immunoloregulation agents represented by a general formula (I), a preparation method, drug compositions containing the immunoloregulation agents, and especially uses of the immunoloregulation agents as immunoloregulation drugs. The compound with characteristics of excellent treatment effect and low toxicity can be used in the fields of immunologic derangement and immunosuppression, and can further be used for treatment of hypoimmunity, organ transplant rejection and autoimmune diseases. The formula I is defined in the instruction.
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Paragraph 0135; 0138; 0139; 0140

(2018/11/22)

One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.
Yamamoto, Takahiro,Togo, Hideo
p. 4187 - 4196
(2018/08/21)

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.
Ma, Chunhua,Miao, Yuqi,Zhao, Minghao,Wu, Ping,Zhou, Jianglu,Li, Zhi,Xie, Xilei,Zhang, Wei
p. 3602 - 3607
(2018/05/26)

An efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes leading to α-halomethyl ketones
A highly efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes has been developed that proceeds smoothly under mild and neutral conditions and provides a general and practical route for the synthesis of a variety of α-halomethyl ketones with high atom-economy, excellent yield, and recyclability of the gold(I) catalyst. The presented method delivers an attractive alternative to classical α-halogenation of ketones.
Hu, Sifan,Liu, Dayi,Yan, Chenyu,Cai, Mingzhong
supporting information
p. 2983 - 2991
(2018/12/04)

Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo
A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.
Dan, Wen-Jia,Tuong, Thi-Mai-Luong,Wang, Da-Cheng,Li, Ding,Zhang, An-Ling,Gao, Jin-Ming
supporting information
p. 2861 - 2864
(2018/07/25)

Novel arylimino thiazole compound, preparation method and uses thereof
The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.
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Paragraph 0144; 0147; 0148; 0149

(2018/03/28)

Antibacterial synergist, preparation method and uses thereof
The present invention relates to an antibacterial synergist, a preparation method and uses thereof, and specifically discloses a compound represented by a formula (I) and having antibacterial synergyactivity, or an optical isomer, a cis-trans isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. The present invention further discloses a medical composition containing the compound, and uses thereof. According to the present invention, the compound can effectively enhance the antibacterial activity of polymyxin B against Acinetobacter baumannii and Klebsiella pneumoniae, and can be used for the antibacterial treatment of pathogenic bacteria insensitive to polymyxin or having low bacterial inhibition activity. The formula (I) is defined in the specification.
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Paragraph 0233; 0234; 0235; 0236

(2018/03/28)

A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone
A new, efficient and green protocol for the one-pot synthesis of α-bromoketones from secondary alcohols using cheap, air stable and non-toxic reagents such as NH4Br and oxone has been developed. This reaction proceeds via two consecutive steps such as oxidation of secondary alcohols and oxidative bromination of in situ generated ketones.
Rammurthy, Banothu,Swamy, Peraka,Naresh, Mameda,Srujana, Kodumuri,Durgaiah, Chevella,Krishna Sai, Gajula,Narender, Nama
p. 3710 - 3714
(2017/07/12)

Method for selective bromination of phenyl alkyl ketone derivatives or phenyl alkyl alcohol derivatives
The present invention refers to phenyl alkyl ketone derivatives or phenyl alkyl alcohol for the preparation of bromide to method are disclosed. Bromination reaction which is an expensive raw material without said number [...] cap, a photocuring liquid bromine (Br) toxic substances toxic to all the remaining wastewater has been exhausted not environment-friendly method are disclosed. In addition, regioselective bromination reaction so as to control, high yield can be undesired compounds. (by machine translation)
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Paragraph 0069; 0087; 0088; 0090

(2018/02/27)

One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
p. 5827 - 5832
(2017/09/09)

Preparation method of 1-(4-bromophenyl)-2-pyridyl-1-yl-1-butanone bromide
The invention relates to a preparation method of 1-(4-bromophenyl)-2-pyridyl-1-yl-1-butanone bromide. The method comprises the following steps of dissolving acetophenone into a certain solvent; performing reaction with liquid bromine at -20 to 40 DEG C according to a certain proportion; preparing 2,4-dibromoacetophenone at 2 to 8 hours; in a certain solvent, performing reaction with a certain proportion of pyridine for 3 to 15 hours at 0 to 80 DEG C; after the reaction is completed, cooling the materials to the room temperature; performing ethyl acetate extraction, water and saturated salt solution washing, anhydrous sodium sulfate drying, rotary evaporation and concentration to obtain a coarse product of the 1-(4-bromophenyl)-2-pyridyl-1-yl-1-butanone bromide; recrystallizing the coarse product to obtain a pure product. The reaction raw materials can be easily obtained; the price is reasonable; the reaction conditions are mild; the operation is easy; the control is easy; the post treatment is simple; the product quality is stable; the purity is high.
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Paragraph 0011

(2017/07/23)

2-amino-5-bromo-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide
The invention relates to a preparation method of 2-amino-5-bromo-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide. The preparation method comprises following steps: acetophenone is dissolved in a certain solvent, acetophenone and liquid bromine react in a certain ratio at the temperature of 20-40 DEG C for 2-8 h, and 2,4-dibromoacetophenone is prepared; 2,4-dibromoacetophenone and 2-amino-5-bromopyridine react in a certain ratio in a certain solvent at the temperature of 0-80 DEG C for 3-15 h, after the reaction, a reactant is cooled to the room temperature, extracted with ethyl acetate, washed with water and a saturated salt solution, dried with anhydrous sodium sulfate and subjected to rotary evaporation and evaporation, a crude product of 2-amino-5-bromo-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide is obtained and is recrystallized, and a pure product is obtained. The preparation method has the advantages as follows: reaction raw materials are relatively available, the price is reasonable, reaction conditions are mild, operation and control are easy, post-treatment is simple, and besides, the product is stable in quality and high in purity.
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Paragraph 0010; 0011; 0012; 0013; 0014; 0015

(2017/08/28)

A method of preparing 2-amino-1-(4-bromophenacyl) methylpyridinium bromide
The invention relates to a method of preparing 2-amino-1-(4-bromophenacyl) methylpyridinium bromide. The method includes steps of dissolving acetophenone into a certain solvent, reacting the acetophenone with bromine in a certain ratio at a temperature ranging from -20 DEG C to 40 DEG C for 2-8 h to prepare 2,4-dibromoacetophenone, reacting the 2,4-dibromoacetophenone with pyridine in a certain ratio in a certain solvent at 0-80 DEG C for 3-15 h, cooling the reaction product to room temperature after the reaction is finished, extracting the reaction product with ethyl acetate, washing the reaction product with water and a saturated salt solution, drying the product with anhydrous sodium sulfate, performing rotary evaporation concentration to obtain a crude 2-amino-1-(4-bromophenacyl) methylpyridinium bromide product, and subjecting the crude product to recrystallization to obtain a high-purity product. According to the method, raw materials are easily available and reasonable in price, reaction conditions are mild, operation and control are easy, after-treatment is simple, and the product is stable in quality and high in purity.
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Paragraph 0011; 0012; 0013; 0014; 0015; 0016

(2017/08/28)

2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide. The preparation method comprises the following steps of dissolving acetophenone in a certain solvent, making the acetophenone react with liquid bromine at subzero 20 to 40 DEG C according to a certain proportion, so as to obtain 2,4-dibromoacetophenone after 2 to 8 hours, in the certain solvent, making the 2,4-dibromoacetophenone react with a certain proportion of 2-amino-3,5-dichloropyridine for 3 to 15 hours at 0 to 80 DEG C, terminating the reaction, cooling an obtained first mixture to room temperature, extracting the first mixture with ethyl acetate, washing a substance through water and saturated salt water, drying the substance with anhydrous sodium sulfate, carrying out rotary evaporation and concentration to subsequently obtain a product provided by the invention, and recrystallizing the coarse product to obtain a pure product. Raw materials in the reaction are relatively easy to obtain; the price is reasonable; the condition of the reaction is mild; the operation is easy; the control is easy; the post treatment is simple; further, the quality of the product is stable; the purity is high.
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Paragraph 0010; 0011; 0012; 0013; 0014; 0015

(2017/08/28)

Preparation method of pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide. The method comprises the following steps: dissolving acetophenone in a certain solvent, and carrying out reaction with liquid bromine according to a certain ratio at -20-40 DEG C for 2-8 hours to obtain 2,4-dibromoacetophenone; in a certain solvent, carrying out reaction with 2-amino-5-iodopyridine according to a certain ratio at 0-80 DEG C for 3-15 hours; after the reaction finishes, cooling to room temperature, extracting with ethyl acetate, washing with water and a saturated saline solution, drying with anhydrous sodium sulfate, and carrying out rotary evaporation concentration to obtain the pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide crude product; and recrystallizing the crude product to obtain the pure product. The method has the advantages of accessible reaction raw materials, reasonable price, mild reaction conditions and simple after-treatment, and is easy to operate and control; and the product has the advantages of stable quality and high purity.
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Paragraph 0010; 0011; 0012; 0013; 0014; 0015

(2017/08/28)

2-amino-5-chloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide
The invention relates to 2-amino-5-chloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide. A preparation method comprises the following steps of dissolving acetophenone in a certain solvent, making the acetophenone react with liquid bromine at -20 to 40 DEG C according to a certain proportion, so as to make 2,4-dibromoacetophenone after 2 to 8 hours, in a certain solvent, making the 2,4-dibromoacetophenone react with 2-aminopyridine with a certain proportion for 3 to 15 hours at 0 to 80 DEG C, terminating the reaction, cooling a reaction product to a room temperature, extracting the reaction product with ethyl acetate, washing the reaction product with water and saturated salt water, drying the reaction product with anhydrous sodium sulfate, carrying out rotary evaporation and concentration on the reaction product to subsequently obtain a 2-amino-5-chloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide crude product, and re-crystallizing the crude product to obtain a pure product. Raw materials of the reaction are relatively easily obtained; the price is reasonable; the conditions of the reaction are mild; the operation is easy; the control is easy; the post treatment is simple; further, the quality of a product is stable; the purity is high.
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Paragraph 0011; 0012; 0013; 0014; 0015

(2017/08/29)

2-amino-5-fluoro-1-(2-(4-bromophenyl)-2-oxyethyl) pyridinium bromide
The invention relates to a preparation method of 2-amino-5-fluoro-1-(2-(4-bromophenyl)-2-oxyethyl) pyridinium bromide. The preparation method comprises the following steps: dissolving acetophenone in a certain solvent, and reacting with liquid bromine under -20 to 40 DEG C according to a certain proportion, thus preparing 2,4-dibromoacetophenone; reacting with a certain proportion of 2-amino-5-fluropyridine in a certain solvent under 0 to 80 DEG C; cooling to room temperature after the reaction; extracting by using ethyl acetate, washing by using water and a saturated salt solution, drying by using anhydrous sodium sulfate, and carrying out rotary evaporation and concentration, thus obtaining a coarse product of the 2-amino-5-fluoro-1-(2-(4-bromophenyl)-2-oxyethyl) pyridinium bromide; recrystallizing the coarse product, thus obtaining a pure product. Reaction raw materials are relatively easy to obtain, the cost is reasonable, the reaction condition is mild, the operation is easy, the control is easy, after-treatment is simple, the product quality is stable, and the purity is high.
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Paragraph 0012; 0013; 0014; 0015; 0016; 0017; 0018; 0019

(2017/08/29)

2-amino-3-bromine-5-chlorin-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2-amino-3-bromine-5-chlorin-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide. The preparation method comprises the following steps: dissolving acetophenone in a certain solvent, enabling acetophenone and liquid bromine to react at a certain proportion at the temperature of minus 20 DEG C to 40 DEG C, obtaining 2,4-dibromoacetophenone after 2-8 hours, enabling 2,4-dibromoacetophenone to react with 2-amino-3-bromine-5-chlorin pyridine at a certain proportion for 3-15 hours in a certain solvent at 0-80 DEG C, finishing the reaction, cooling to the room temperature, extracting with ethyl acetate, washing with water and saturated salt solution, drying with anhydrous sodium sulfate, rotatably evaporating, and concentrating to obtain a crude product of 2-amino-3-bromine-5-chlorin-1-(2-(4-bromophenyl)-2-oxoethyl) pyridinium bromide. The crude product is recrystallized to obtain a pure product. The reaction materials are relatively easy to get, the price is reasonable, the reaction conditions are mild, the preparation method is easy to operate and easy to control, the postprocessing is simple, the product quality is stable, and the purity is high.
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Paragraph 0011; 0012; 0013; 0014; 0015

(2017/08/29)

Catalytic dehydrogenative dual functionalization of ethers: Dealkylation-oxidation-bromination accompanied by C-O bond cleavage: Via aerobic oxidation of bromide
Catalytic dehydrogenative dual functionalization (DDF) of ethers via oxidation, dealkylation, and α-bromination by the aerobic oxidation of bromide was developed to obtain the corresponding α-bromo ketones in high yields. In particular, the reaction of substituted tetrahydrofurans as cyclic ethers provided 3,3-dibromo tetrahydrofuran-2-ols in high yields selectively through the double α-bromination.
Moriyama, Katsuhiko,Hamada, Tsukasa,Nakamura, Yu,Togo, Hideo
supporting information
p. 6565 - 6568
(2017/07/10)

Water-controlled selective preparation of α-mono or α,α′-dihalo ketones: Via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.
Wu, Chao,Xin, Xiu,Fu, Zhi-Min,Xie, Long-Yong,Liu, Kai-Jian,Wang, Zheng,Li, Wenyi,Yuan, Zhi-Hui,He, Wei-Min
p. 1983 - 1989
(2017/06/09)

AuIII-Catalyzed Formation of α-Halomethyl Ketones from Terminal Alkynes
A AuIII-catalyzed synthesis of α-halomethyl ketones from terminal alkynes was developed. This approach features excellent functional group compatibility and good yields for both aromatic and aliphatic terminal alkynes. The resulting α-halomethyl ketones were used to prepare heterocyclic indolizine structures. The plausible mechanism of the one-pot reaction is proposed.
Xing, Yalan,Zhang, Ming,Ciccarelli, Sarah,Lee, John,Catano, Bryant
supporting information
p. 781 - 785
(2017/02/15)

1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
A variety of terminal alkenes were converted to the corresponding amides in yields of 25 to 86% in water via treatment with 1,3-dibromo-5,5-dimethylhydantoin, followed by reaction with molecular iodine and aq. NH3 (or amine) in one pot. This metal- and organic solvent-free protocol is not only suitable for styrene derivatives, but also, for the first time, works well on terminal aliphatic alkenes.
Ma, Chunhua,Fan, Guojie,Wu, Ping,Li, Zhi,Zhou, Yang,Ding, Qingjie,Zhang, Wei
p. 9889 - 9894
(2017/12/12)

Design, synthesis and in vitro cytotoxicity studies of novel β-carbolinium bromides
A series of novel β-carbolinium bromides has been synthesized from easily accessible β-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 16l, 16o and 16s exhibited potent anticancer activity with IC50values of 50= 3.16–7.93 μM). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 16l and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that β-carbolinium salts induce apoptosis in these cells. Additionally, the most potent β-carbolines 16l and 16s were found to inhibit tubulin polymerization.
Venkataramana Reddy,Mishra, Shriprada,Tantak, Mukund P.,Nikhil, Kumar,Sadana, Rachna,Shah, Kavita,Kumar, Dalip
supporting information
p. 1379 - 1384
(2017/03/08)

TsNBr2mediated oxidative functionalization of alkynes
A new approach has been developed for oxidative transformation of alkynes by controlled manipulation of TsNBr2mediated process. Alkynes could be readily converted to ketones and α-bromoketones via an oxybromination–debromination sequence. When alkynes are treated successively with TsNBr2, KI and Na2SO3in a mixture of acetone and water at room temperature, corresponding ketones were obtained. On the other hand, treatment of alkynes with TsNBr2and Na2SO3in a mixture of ethyl acetate, acetone and water at room temperature could produce corresponding α-bromoketones. 1-Bromoalkynes could also be synthesized from corresponding alkynes within a very short time using TsNBr2at room temperature. In all cases, excellent yields of corresponding products are obtained.
Rajbongshi, Kamal Krishna,Hazarika, Debojit,Phukan, Prodeep
p. 4151 - 4158
(2016/07/06)

Dual oxidation/bromination of alkylbenzenes
In the presence of sodium bromide and Oxone, a range of alkylbenzene derivatives are brominated and/or oxidized with up to four C-H bonds being functionalized.
Aborways, Marwa M.,Moran, Wesley J.
supporting information
p. 983 - 985
(2016/02/16)

1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water
α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.
Xu, Senhan,Wu, Ping,Zhang, Wei
p. 11389 - 11395
(2016/12/18)

One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant followed by trapping with suitable nucleophiles to provide imidazopyridines and thiazoles.
Shinde, Mahesh H.,Kshirsagar, Umesh A.
supporting information
p. 1455 - 1458
(2016/04/04)

First Catalyzed Hydration of Haloalkynes by a Recyclable Catalytic System
The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also be scaled up.
Zou, Huaxu,He, Weibao,Dong, Qizhi,Wang, Ruijia,Yi, Niannian,Jiang, Jun,Pen, Dongming,He, Weimin
p. 116 - 121
(2016/01/26)