- Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
-
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
- Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
-
supporting information
p. 15117 - 15127
(2021/10/25)
-
- Synthesis of Aza[ n]phenacenes (n = 4-6) via Photocyclodehydrochlorination of 2-Chloro- N-aryl-1-naphthamides
-
A novel methodology for the synthesis of aza[n]phenacenes was successfully developed utilizing photocyclodehydrochlorination reaction of 2-chloro-N-aryl-1-naphthamides. In these key intermediates, the factors influencing the photoreaction were studied. The target aza[n]phenacenes were obtained by triflation or chlorination from prepared phenanthridinones, followed by hydrogenation. The introduction of a nitrogen atom into a phenacene skeleton induced changes in the physicochemical properties. The important properties of prepared aza[n]phenacenes (n = 4-6) were studied experimentally and by density functional theory calculations and were compared to those of their carbo analogues. Furthermore, some important features of the crystalline aza[n]phenacenes were investigated, including intermolecular interaction in the crystal lattice and the increased solubility or decreased melting points.
- Váňa, Lubomír,Jakubec, Martin,Sykora, Jan,Císa?ová, Ivana,Storch, Jan,Církva, Vladimír
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p. 13252 - 13264
(2021/10/01)
-
- Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
-
A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.
- Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
-
supporting information
p. 4843 - 4848
(2021/06/28)
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- α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
-
Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
- Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
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p. 7433 - 7445
(2020/06/27)
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- The use of Cr (CO)6 as an alternative CO source in Pd-catalyzed C-N bond formation: Synthesis of benzamides
-
An efficient strategy for the synthesis of benzamides from acetamides and aryl iodides using 1?mol% Pd (OAc)2 as catalyst and Cr (CO)6 as CO-precursor is described. This new synthetic methodology displays high functional group tolerance on both substrates and avoids the need for ligands, reducing agents, or other additives. The corresponding products were obtained in good to excellent yields at atmospheric pressure under mild reaction conditions.
- Mozaffari, Mozhdeh,Nowrouzi, Najmeh,Abbasi, Mohammad
-
-
- Metal-Free Sustainable Synthesis of Amides via Oxidative Amidation Using Graphene Oxide as Carbocatalyst in Aqueous Medium
-
Abstract: We describe an efficient, clean and metal-free procedure for the synthesis of amides via oxidative amidation of aldehydes with anilines using graphene oxide (GO) as a recyclable catalyst and KBrO3 as a mild oxidant in aqueous medium under microwave irradiation. GO nanosheets were prepared and characterized by XRD, TEM, SEM, and FT-IR, analyses. GO showed high compatibility with KBrO3 in water and offered high TOF value (1.30 × 10?3 mol?g?1 min?1). GO oxygen functionalities catalyze the oxidative amidation effectively in mild condition with high recyclability. A plausible mechanism was proposed by the isolating the intermediate. Graphic Abstract: [Figure not available: see fulltext. ]
- Dandia, Anshu,Parihar, Sonam,Saini, Pratibha,Rathore, Kuldeep S.,Parewa, Vijay
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p. 3169 - 3175
(2019/07/30)
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- Method for synthesizing amide compound through photocatalysis in water phase
-
The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
- -
-
Paragraph 0018-0027
(2019/10/01)
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- Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
-
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
- Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
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p. 4087 - 4101
(2019/04/30)
-
- AGRICULTURAL CHEMICALS
-
The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.
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-
Page/Page column 100; 101
(2019/08/08)
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- Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
-
Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
- Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
-
supporting information
p. 237 - 241
(2019/01/10)
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- Palladium-catalyzed intramolecular C-H arylation of 2-halo-: N -Boc- N -arylbenzamides for the synthesis of N-H phenanthridinones
-
A palladium catalyzed synthesis of N-H phenanthridinones was developed via C-H arylation. The protocol gives phenanthridinones regioselectively by one-pot reaction without deprotection. It exhibits broad substrate scope and affords targets in up to 95% yields. Importantly, it could be applied for the less reactive o-chlorobenzamides.
- Hu, Quan-Fang,Gao, Tian-Tao,Shi, Yao-Jie,Lei, Qian,Yu, Luo-Ting
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p. 13879 - 13890
(2018/04/25)
-
- Design, Synthesis, and Pharmacological Activity of a New Matrix Metalloproteinase-9 Inhibitor
-
The new MMP-9 inhibitor 1-{4-[(4-chlorobenzoyl)amino]phenyl}sulfonyl-L-proline, with a theoretical inhibition constant of IC50 = 4 × 105 M, was constructed on the basis of structural requirements for selective inhibitors of gelatinases. This constructed compound and its close structural analogs were synthesized and these substances were found to have low toxicity, (LD50 > 300 mg/kg). The new inhibitor given p.o. at a dose of 20 mg/kg/day on the background of acute myocardial infarction significantly decreased the content of immunoreactive MMP-9 in plasma in rats, to the level obtained with doxycycline.
- Grigorkevich,Mokrov,Dyabina,Stolyaruk,Tsorin,Ionova,Kryzhanovskii,Gudasheva,Durnev
-
-
- Synthesis of N-acetoxy-N-arylamides via diacetoxyiodobenzene promoted double acylation reaction of hydroxylamines with aldehydes
-
A facile and efficient synthesis of N-acetoxy-N-arylamides through double acylations of hydroxylamines with aldehydes and diacetoxyiodobenzene is reported. The yields of the products are good to excellent.
- Zhang, Huaiyuan,Su, Yingpeng,Wang, Ke-Hu,Huang, Danfeng,Li, Jun,Hu, Yulai
-
supporting information
p. 5337 - 5344
(2017/07/10)
-
- Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides
-
A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.
- Liu, Hailong,Han, Weibiao,Li, Chun,Ma, Zhiyong,Li, Ruixiang,Zheng, Xueli,Fu, Haiyan,Chen, Hua
-
supporting information
p. 389 - 393
(2016/02/18)
-
- Detection of weak hydrogen bonding to fluoro and nitro groups in solution using H/D exchange
-
Hydrogen/deuterium (H/D) exchange can be a sensitive technique for measuring the strength of hydrogen bonding to neutral organic nitro and fluoro groups. The slower rates of reaction in comparison to suitable controls suggest that hydrogen bonding is present, albeit rather weak.
- Shugrue,Defrancisco,Metrano,Brink,Nomoto,Linton
-
supporting information
p. 2223 - 2227
(2016/03/01)
-
- Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors
-
Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.
- Fang,Tranmer
-
supporting information
p. 720 - 724
(2016/05/19)
-
- Efficient one-stage procedure of Beckmann ketones rearrangement in the presence of hydroxylamine
-
Ketoximes formed from ketones in the presence of hydroxylamine and silica gel in formic acid undergo in situ the Beckmann rearrangement under mild conditions affording in high yields the corresponding amides. Unsymmetrical aromatic ketones, methyl aryl ketones, and methyl cyclohexyl ketone under these conditions form as a rule amides mixtures.
- Kuksenok,Shtrykova,Filimonov,Sidel'nikova
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p. 196 - 199
(2016/04/19)
-
- Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation
-
A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.
- Seo, Hong-Ahn,Cho, Yeon-Ho,Lee, Ye-Sol,Cheon, Cheol-Hong
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p. 11993 - 11998
(2016/01/09)
-
- Polyethylene glycol as a recyclable reaction medium for gold-catalysed direct oxidative amide synthesis from aldehydes and amines
-
Polyethylene glycol (PEG) was used as the recyclable reaction medium for gold-catalysed oxidative amidation of aldehydes with amines by using tert-butyl hydroperoxide (TBHP, 70% aqueous) as the oxidant. The reaction proceeded efficiently to provide the corresponding products in moderate to good yields under mild conditions. Both the catalysts and solvent can be easily recovered and reused by simple extraction without significant loss of activity.
- Jiang, Hui-Liang,Zhao, Jie
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p. 654 - 656
(2016/01/25)
-
- Synthesis of amides through an oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions
-
A simple, inexpensive and efficient one-pot synthesis of amides was achieved in good yields via the direct oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions.
- Du, Juan,Luo, Kai,Zhang, Xiuli
-
p. 54539 - 54546
(2015/01/09)
-
- Facile access to amides and hydroxamic acids directly from nitroarenes
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A new method for synthesis of amides and hydroxamic acids from nitroarenes and aldehydes is described. The MnO2 catalyzed thermal deoxygenation of nitrobenzene resulted in formation of a reactive nitroso intermediate which on reaction with aldehydes provided amides and hydroxamic acids. The thermal neat reaction in the presence of 0.01 mmol KOH predominantly led to formation of hydroxamic acid whereas reaction in the presence of 1 mmol acetic acid produced amides as the only product. the Partner Organisations 2014.
- Jain, Shreyans K.,Aravinda Kumar,Bharate, Sandip B.,Vishwakarma, Ram A.
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p. 6465 - 6469
(2014/08/18)
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- Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water
-
A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)·2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
-
supporting information
p. 7478 - 7481
(2014/12/11)
-
- An efficient synthesis of amides from alcohols and azides catalyzed by a bifunctional catalyst Au/DNA under mild conditions
-
A novel Au/DNA-catalyzed amidation from alcohols and azides was developed under mild conditions. Taking advantage of the water-soluble reversibility of this catalyst, the transformation could be carried out smoothly in water and the catalyst could be recovered and reused by a simple phase separation. This amidation reaction unitized the hydrogen transfer process and the oxidative coupling process synergistically in an atom economical and environmentally benign synthesis. the Partner Organisations 2014.
- Guo, Xuefeng,Tang, Lin,Yang, Yu,Zha, Zhenggen,Wang, Zhiyong
-
supporting information
p. 2443 - 2447
(2014/05/06)
-
- HETEROCYCLIC COMPOUNDS AND USES THEREOF
-
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including P13 kinase activity, are described herein.
- -
-
Paragraph 0738; 0739; 0692; 0693; 0694; 1015
(2013/03/26)
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- Direct N-cyclopropylation of secondary acyclic amides promoted by copper
-
The N-cyclopropylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper system. The corresponding tertiary acyclic amides, which constitute a wide family of biologically active compounds, have been obtained in good to excellent yields.
- Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
-
supporting information
p. 7412 - 7414
(2013/09/23)
-
- A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
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An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
- Balkrishna, Shah Jaimin,Kumar, Sangit
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p. 1417 - 1426
(2012/06/30)
-
- Synthesis and antifungal activity of 2-Chloro-N-phenylbenzamide
-
In the present study, 2-chloro-N-phenylbenzamide was synthesized by the ammonolysis of 2-chlorobenzoyl chloride. Its structure was confirmed by IR and 1H NMR. Its antifungal activity against Sclerotinia sclerotiorum and Botrytis cinerea has bee
- Tang, Xiaorong,Chen, Shaoling,Wang, Ling
-
experimental part
p. 2860 - 2862
(2012/08/28)
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- Optimization and antifungal activity of chalcone analogues
-
Using chalcone as a leading compound, a series of its analogues (compounds 1-16) were designed and synthesized. Their activity of antipathogenic fungi of plants has been evaluated in the laboratory. The results showed that these compounds had certain antifungal activity against Sclerotinia sclerotiorum and Botrytis cinerea. Among them, the inhibition of growth for 2-chloro-N- phenylbenzamide (compound 2) reached 92.6 and 90.1 % at a concentration of 100 mg L-1, respectively.
- Tang, Xiaorong,Chen, Shaoling,Wang, Ling
-
experimental part
p. 2516 - 2518
(2012/09/08)
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- Highly efficient amide synthesis from alcohols and amines by virtue of a water-soluble gold/DNA catalyst
-
Gold takes to water: The synthesis of amides directly from alcohols and amines was realized by using a water-soluble Au/DNA nanohybrid as the catalyst. The interactions between the gold nanoparticles, DNA, and water lead to high catalytic efficiency under mild reaction conditions. The wide substrate scope includes less-basic aromatic amines, and this catalyst is recyclable.
- Wang, Ye,Zhu, Dapeng,Tang, Lin,Wang, Sujing,Wang, Zhiyong
-
supporting information; experimental part
p. 8917 - 8921
(2011/10/31)
-
- Nano sulfated titania as solid acid catalyst in direct synthesis of fatty acid amides
-
Nanosized sulfated titania was prepared by a sol-gel hydrothermal process. X-ray diffraction (XRD), transmission electron, and scanning electron micrographs (TEM and SEM), FT-IR specific surface area, and BET N2 adsorption were employed to characterize the properties of the synthesized sulfated TiO2. The results indicate that both anatase and rutile TiO2 are obtainable. This prepared sulfated titania showed high catalytic activity in direct amidation of fatty acids as well as benzoic acids with various amines under solvent-free conditions.
- Hosseini-Sarvari, Mona,Sodagar, Esmat,Doroodmand, Mohammad Mahdi
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supporting information; experimental part
p. 2853 - 2859
(2011/05/17)
-
- A simple copper-catalyzed synthesis of tertiary acyclic amides
-
The N-arylation of aromatic and aliphatic secondary acyclic amides, known to be poor nucleophiles, has been accomplished using a simple and cheap copper catalytic system. The corresponding tertiary acyclic amides, which can be found in numerous biologically active compounds, have been obtained in good to excellent yields.
- Racine, Emilie,Monnier, Florian,Vors, Jean-Pierre,Taillefer, Marc
-
supporting information; experimental part
p. 2818 - 2821
(2011/07/09)
-
- Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents
-
Substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized. The results of preliminary screening revealed that these compounds are potent in killing solid tumor cancers.
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Page/Page column 7
(2008/06/13)
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- Infrared spectra of N-aryl substituted amides 2/4-XC6H 4NHCOR (R = H, CH3-iXi, C6H 5 or C6H5Cl; X = H, Cl or CH3 and i = 0, 1, 2 or 3)
-
Several N-(aryl)-substituted amides of the general formula, 2/4-XC 6H4NHCOR (where X = H, Cl or CH3 and R = H, CH3, CH2CH3, CH(CH3)2, C(CH3)3, C6H5 or C6H 5Cl) are prepared, characterised and their infrared spectra measured in the solid state and analysed. Generally chloro substitution in the side chain increases the C=O absorptions, while that of methyl groups lower the wave numbers. Amides with trimethyl substituted side chains absorb at higher wavenumbers. But the N-H and C-N stretching vibrations do not show particular trends on side chain substitution. This may be due to the fact that the spectra were recorded in the solid state and the compounds may crystallise in different forms in the solid state. The intercorrelations of C=O and N-H absorption frequencies of all the amides have been made. The correlations are reasonably linear with some exceptions for the reasons stated above.
- Gowda, B. Thimme,Jyothi,Jayalakshmi,Damodara
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p. 564 - 568
(2007/10/03)
-
- A series of new zirconium complexes bearing bis(phenoxyketimine) ligands: Synthesis, characterization and ethylene polymerization
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A series of new zirconium complexes bearing bis(phenoxyketimine) ligands, bis((3,5-di-tert-butyl-C6H2-2-O)R1CN (2-R 2-C6H4))ZrCl2 {R1 = Me, R2 = H (2a); R1 = Et, R2 = H (2b); R 1 = Ph, R2 = H (2c); R1 = 2-Me-Ph, R 2 = H (2d); R1 = 2-F-Ph, R2 = H (2e); R 1 = 2-Cl-Ph, R2 = H (2f); R1 = 2-Br-Ph, R 2 = H (2g); R1 = Ph, R2 = Me (2h); R 1 = Ph, R2 = F (2i)}, have been prepared, characterized and tested as catalyst precursors for ethylene polymerization. Crystal structure analysis reveals that complex 2c has a six coordinate center in a distorted octahedral geometry with trans-O, cis-N, cis-Cl arrangement which possesses approximate C2 symmetry. When activated with methylaluminoxane (MAO), complexes 2a-2i exhibited high ethylene polymerization activities of 10 6-108 g PE (mol M h)-1. Compared with the bis(phenoxyimine) zirconium analogues bis((3,5-di-tert-butyl-C6H 2-2-O)CHNC6H5)ZrCl2 (3), the introduction of substituent on the carbon atom of the imine double bond enhanced the catalytic activity and molecular weight of prepared polyethylene. Especially, when the H atom at the carbon atom of the imine double bond was replaced by 2-fluoro-phenyl with strong electronic-withdrawing property, complex 2e displayed the highest catalytic activity, and the polyethylene obtained possessed the highest molecular weight and melt point.
- Chen, Shangtao,Zhang, Xiaofan,Ma, Hongwei,Lu, Yingying,Zhang, Zhicheng,Li, Huayi,Lu, Zhanxia,Cui, Nannan,Hu, Youliang
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p. 4184 - 4191
(2007/10/03)
-
- Control of the fading properties of photochromic 3,3-diaryl-3H-naphtho[2,1-b]pyrans
-
The synthesis and spectroscopic properties of some novel photochromic 3H-naphtho[2,1-b]pyrans are reported. Varying the size of an ortho-substituent on one of the geminal aryl rings allows the rate of fade of the photogenerated color to be controlled.
- Gabbutt, Christopher D.,Heron, B. Mark,Instone, Alicia C.
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p. 843 - 855
(2007/10/03)
-
- Activation of the aryl hydrocarbon receptor by methyl yellow and related congeners: structure-activity relationships in halogenated derivatives.
-
The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure-activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2'- and 6'-position), and reduction by substitution at the para-position (4'-position). The greatest enhancement of the ligand activity was observed in 2',6'-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4'-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2')-chlorine-substitution, and the AhR ligand activity of 2',4'-dichlorobenzanilide was similar to that of 2'-chloro-MY. These results suggest that the amide bond is equivalent to the -N=N- or -CH=CH- double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.
- Kato, Taka-aki,Matsuda, Tomonari,Matsui, Saburo,Mizutani, Takaharu,Saeki, Ken-ichi
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p. 466 - 471
(2007/10/03)
-
- 7-(4,6-dimethoxypyrimidinyl)oxy- and -thiophthalides as novel herbicides: Part 1. CGA 279 233: A new grass-killer for rice
-
A series of novel types of 7-(4,6-dimethoxypyrimidin-2-yl)oxy - and -thio-3-methyl-1 (3H)-isobenzofuranones were discovered at Dr R Maag AG. From the thio-isobenzofuranyl series, CGA 279 233 - BSI-proposed common name pyriftalid - was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid-derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico-chemical behaviour.
- Luethy, Christoph,Zondler, Helmut,Rapold, Thomas,Seifert, Gottfried,Urwyler, Bernhard,Heinis, Thomas,Steinruecken, Hans Christian,Allen, James
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p. 205 - 224
(2007/10/03)
-
- Phase-transfer-catalyzed synthesis of N-aryl-N'-(2-chlorobenzoyl)-thiourea derivatives
-
Reaction of aromatic amines with 2-chlorobenzoyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-400 (PEG-400) as the catalyst yielded N-aryl-N'-(2-chlorobenzoyl)thioureas 3a-3j in g
- Zhang, Youming,Wei, Taibao,Wang, Lailai
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p. 751 - 756
(2007/10/03)
-
- Method for producing alkylsulfinylbenzamides and 1,2-benzisothiazol-3-ones
-
A method for producing an alkylthiobenzamide by carrying out a reaction of a halobenzamide with an alkanethiol in the presence of a base in a heterogeneous solvent; a method for producing an alkylsulfinylbenzamide by carrying out a reaction of an alkylthi
- -
-
-
- Diazotisation Rearrangement of Tosylhydrazones of ortho- and meta-Substituted-benzophenones and α-Substituted-acetophenones (Synthesis of Anilides)
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Ortho and meta-substituted-benzophenones (1a-g) and substituted-acetophenones (1h-i) were converted into tosylhydrazones (2a-i) by reacting with p-toluenesulphonyl-hydrazide.Conversion of 2a-i to the anilides (3a-i) was effected with the reagents H2SO4 and NaNO2, and was found to be as facile as in case of the para-substituted-benzophenone hydrozones.
- Joshi, Vidya,Sharma, R. K.
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p. 564 - 566
(2007/10/02)
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- o-CHLOROTHIOBENZAMIDES AS ADDITIVES TO LUBRICATING OILS.
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The authors report the results of synthesis of o-chlorothiobenzamides and of a study of their properties as lubricant additives. The results of tests of the anticorrosion properties of o-chlorothiobenzamides were compared with the results of tests on compounds of analogous structure: thiobenzamides and o-chlorobenzamides. The results show that o-chlorothiobenzamides added to DS-11 oil have definite anticorrosion and antiwear effects, manifested in decrease of the degree of corrosion and of the diameter of the wear patch (D//p).
- Kuliev,Kurbanov,Mamedov,Kuliev
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p. 139 - 142
(2007/10/02)
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- N-Tetrachloroethylthio benzoyl anilides useful as acaricides and to control mosquitoes
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N-tetrachloroethylthio benzoyl anilide compounds having the formula STR1 in which R is chlorine, hydrogen, or trifluoromethyl and X is hydrogen or fluorine, useful as acaricides and to control mosquitoes.
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- Reaction Pathways for Arylcarbamoyl Radicals and the Cyclization of o-Substituted Phenylcarbamoyl Radicals
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N-Arylcarbamoyl radicals generated from N-arylformamides with di-t-butyl peroxide (ButOOBut) in chlorobenzene at 110 deg C give rise to a series of reactions depending on the nature and the position of the substituent in the aromatic ring.When the aryl group is phenyl or p-chlorophenyl the following reactions on carbamoyl radicals occur: (i) loss of hydrogen with formation of aryl isocyanates, whereas the loss of carbon monoxide leads to arylamines via arylaminyl radicals; (ii) dimerization to NN'-diaryloxamides; (iii) aromatic substitution on chlorobenzene leading to N-arylbenzamides (ipso-substitution) and N-arylchlorobenzamides.The isocyanates trapped by t-butyl alcohol and arylamines give t-butyl N-arylcarbamates and NN'-diarylureas.With o-substituted N-phenylformamides intramolecular cyclization is observed as well; in fact, the N-(o-cyanophenyl)formamide affords isatin via addition of the carbamoyl radical to the cyano-group while the N-formamide gives 2-benzothiazolone and phenyl radicals through an SHi reaction on the sulphur atom; finally 2-formamidobiphenyls furnish phenanthridones in very high yields.
- Leardini, Rino,Tundo, Antonio,Zanardi, Giuseppe
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p. 3164 - 3167
(2007/10/02)
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- 3-Substituted-4-aryl isoquinolines
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3-Substituted-4-aryl isoquinolines, e.g. 3-tertiary butyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline, prepared from corresponding isoquinoline intermediates, are useful as anti-diabetic agents.
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