- On the origins of stereoselectivity in the aminocatalytic remote alkylation of 5-alkylfurfurals
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In the manuscript, computational studies on the remote alkylation of 5-alkylfurfurals proceeding via formation of the corresponding trienamine intermediate are presented. By the means of density functional theory (DFT) calculations and the symmetry-adapte
- Dyguda, Mateusz,Przydacz, Artur,Krzemińska, Agnieszka,Albrecht, ?ukasz
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Read Online
- Method for reducing carbonyl reduction to methylene under illumination
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The invention belongs to the technical field of organic chemical synthesis. The method comprises the following steps: (1) mixing the carbonyl compound and the amine compound in a solvent, reacting 3 - 6 under the illumination of 380 - 456 nm, the reaction system is low in toxicity, high in atom utilization rate 12 - 24h. and production efficiency, safe and controllable in reaction process and capable of simplifying the operation in the preparation and production process. At the same time, the residue toxicity of the reaction is minimized, the pollution caused by the production process to the environment is reduced, and the steps and operations of removing residues after the reaction are simplified. In addition, the reactant feedstock is readily available. The reactant does not need additional modification before the reaction, can be directly used for preparing production, simplifies the operation steps, and shortens the reaction route. The production cost is obviously reduced.
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Paragraph 0033-0038; 0145-0149
(2021/09/29)
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- Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst
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The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co
- Antonietti, Markus,Ghosh, Indrajit,K?nig, Burkhard,Khamrai, Jagadish,Savateev, Aleksandr
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p. 3526 - 3532
(2020/04/09)
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- Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions
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Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.
- La Manna, Pellegrino,Soriente, Annunziata,De Rosa, Margherita,Buonerba, Antonio,Talotta, Carmen,Gaeta, Carmine,Neri, Placido
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p. 1673 - 1683
(2019/03/26)
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- Electrochemical Hydrogenation with Gaseous Ammonia
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As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
- Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
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supporting information
p. 1759 - 1763
(2019/01/16)
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- Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
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A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
- Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
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supporting information
(2019/05/07)
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- Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules
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A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.
- La Manna, Pellegrino,Talotta, Carmen,Floresta, Giuseppe,De Rosa, Margherita,Soriente, Annunziata,Rescifina, Antonio,Gaeta, Carmine,Neri, Placido
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p. 5423 - 5428
(2018/04/09)
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- Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant
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A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has been developed using a homolytic C-O bond cleavage protocol that has recently been established. The treatment of a benzyl alcohol and aryl halide with a nickel catalyst and low-valent titanium reagent generated from TiCl4(lutidine) (lutidine = 2,6-lutidine) and manganese powder afforded the cross-coupled product in high yield. A mechanistic study indicated the intermediacy of the benzyl radicals that originate from the benzyl alcohols.
- Suga, Takuya,Ukaji, Yutaka
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p. 7846 - 7850
(2019/01/14)
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- Substrate switchable Suzuki-Miyaura coupling for benzyl ester: Vs. benzyl halide
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Two reaction conditions were developed to accomplish the substrate switchable Suzuki-Miyaura coupling of benzyl derivatives and arylboronic acid derivatives. Under conditions for esters, benzyl esters such as carbonates and acetates reacted with arylboronic acids to afford the corresponding diarylmethanes. However, the benzyl halides did not react under the same conditions. On the other hand, benzyl halides such as bromides and chlorides furnished diarylmethanes under conditions for halides, under which benzyl ester substrates did not react, in which water was found to play an important role. This switching system was tested using the intermolecular/intramolecular competitive reactions, during which the desired products could be synthesized by selecting the appropriate reaction conditions.
- Ohsumi, Masato,Ito, Akitaka,Nishiwaki, Nagatoshi
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p. 35056 - 35061
(2018/10/24)
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- Nickel-catalyzed cross-coupling of aldehydes with aryl halides: Via hydrazone intermediates
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Traditional cross-couplings require stoichiometric organometallic reagents. A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed, merging the Wolff-Kishner reduction and the classical cross-coupling reactions. Aromatic aldehydes, aryl iodides and aryl bromides are especially effective in this new cross-coupling chemistry.
- Tang, Jianting,Lv, Leiyang,Dai, Xi-Jie,Li, Chen-Chen,Li, Lu,Li, Chao-Jun
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supporting information
p. 1750 - 1753
(2018/02/21)
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- Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions
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Bench-stable solid triorganoindium compounds have been prepared by coordination with 4-(dimethylamino)pyridine (DMAP). The solid R3In(DMAP) complexes are obtained from the corresponding solution of R3In in quantitative yield and can
- Gil-Negrete, José M.,Pérez Sestelo, José,Sarandeses, Luis A.
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supporting information
p. 1453 - 1456
(2018/02/19)
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- Synthetic method of diarylmethanes
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The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.
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Paragraph 0186; 0187; 0188; 0189; 0190
(2017/08/28)
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- Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions
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The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki-Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of C-SO2 bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked versus common electrophiles and its use in iterative cross-couplings for concise synthesis of biologically active molecules is described.
- Nambo, Masakazu,Keske, Eric C.,Rygus, Jason P. G.,Yim, Jacky C.-H.,Crudden, Cathleen M.
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p. 1108 - 1112
(2017/08/09)
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- Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts
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We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.
- Wu, Guojiao,Xu, Shuai,Deng, Yifan,Wu, Chaoqiang,Zhao, Xia,Ji, Wenzhi,Zhang, Yan,Wang, Jianbo
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p. 8022 - 8030
(2016/11/19)
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- Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides
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A new protocol for the direct reductive cobalt-catalyzed arylation of benzyl chlorides has been developed in order to form functionalized diarylmethanes. A variety of reactive groups either on the aryl or the benzyl halide was employed. This represents the first cobalt-catalyzed reductive cross-coupling which does not require any ligand and pyridine. A reaction pathway is proposed involving a radical benzyl species. (Figure presented.).
- Pal, Suman,Chowdhury, Sushobhan,Rozwadowski, Elodie,Auffrant, Audrey,Gosmini, Corinne
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p. 2431 - 2435
(2016/08/16)
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- Iron-catalyzed arylation of aromatic ketones and aldehydes mediated by organosilanes
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A simple and efficient iron-catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4-% FeCl3 or Fe(acac) 3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel-Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel-Crafts alkylation reactions, robust applications for the synthesis of pharmaceutical intermediates and so on can be envisioned. A robust one-pot, iron-catalyzed chlorination Friedel-Crafts alkylation reaction of benzylic carbonyl compounds, mediated by chlorotrimethylsilane and triethylsilane, has been developed to yield substituted diaryl and triaryl building blocks. Copyright
- Savela, Risto,Majewski, Marcin,Leino, Reko
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p. 4137 - 4147
(2014/07/08)
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- Palladium-catalyzed synthesis of heterocycle-containing diarylmethanes through suzuki-miyaura cross-coupling
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The heterocycle-containing diarylmethane synthesis from chloromethyl(hetero)arenes with (hetero)arylboron reagents was attained using the palladium/ether-imidazolium chloride system. This coupling process tolerated a diverse range of heteroaromatic moieties with sufficient catalytic activity to achieve the efficient synthesis of various diheteroarylmethanes in good to excellent yields.
- Kuriyama, Masami,Shinozawa, Mina,Hamaguchi, Norihisa,Matsuo, Seira,Onomura, Osamu
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p. 5921 - 5928
(2014/07/08)
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- Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O
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An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.
- Li, Yu,Xiong, Yan,Li, Xueming,Ling, Xuege,Huang, Ruofeng,Zhang, Xiaohui,Yang, Jianchun
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p. 2976 - 2981
(2014/06/10)
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- Suzuki-miyaura cross-couplings mediated by trans-PdBr(N-Succ)(PPh 3)2: A convenient synthetic method for diarylmethanes and aryl(heteroaryl)- methanes
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Diarylmethanes can be accessed efficiently by Suzuki-Miyaura cross-couplings of arylboronic acids with benzyl halides mediated by trans-PdBr(N-Succ) (PPh3)2. The methodology can be applied to the synthesis of aryl(heteroaryl)methanes. Georg Thieme Verlag Stuttgart New York.
- Fairlamb, Ian J. S.,Sehnal, Petr,Taylor, Richard J. K.
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experimental part
p. 508 - 510
(2009/07/11)
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- One-pot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine and -[1,2-b]pyridazine by Suzuki-Miyaura cross-coupling reactions
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A very simple, mild and inexpensive palladium-catalyzed cross-coupling of (hetero)arylboronic acids with benzylic halides occurs in good yield. This method was successfully expanded to two heterocyclic electrophiles and allowed onepot dual substitutions of bromobenzyl chloride, 2-chloromethyl-6- halogenoimidazo[1,2-a]pyridine or -[1,2-b]pyridazine, leading to numerous new unsymmetrical methylenelinked biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Henry, Nicolas,Enguehard-Gueiffier, Cecile,Thery, Isabelle,Gueiffier, Alain
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supporting information; experimental part
p. 4824 - 4827
(2009/05/07)
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- Benzylation of arenes through FeCl3-catalyzed Friedel-Crafts reaction via C-O activation of benzyl ether
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Various benzyl ethers were converted to benzyl arenes via a FeCl3-catalyzed Friedel-Crafts alkylation reaction under mild condition in good yields. This method also offered a simple and practical approach to synthesize di- or tri-aryl methanes and aryl heteroaryl methanes through the activation of C-O bonds.
- Wang, Bi-Qin,Xiang, Shi-Kai,Sun, Zuo-Peng,Guan, Bing-Tao,Hu, Ping,Zhao, Ke-Qing,Shi, Zhang-Jie
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p. 4310 - 4312
(2008/09/21)
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- Cross-coupling reaction of allylic and benzylic carbonates with organo[2-(hydroxymethyl)phenyl]dimethylsilanes
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The title reaction is found to proceed in the presence of a palladium catalyst and in the absence of any activator. Various functional groups are tolerated to give a diverse range of 1,4-diene and diarylmethane products, which are ubiquitous units of natural products and pharmaceuticals. Copyright
- Nakao, Yoshiaki,Ebata, Shiro,Chen, Jinshui,Imanaka, Hidekazu,Hiyama, Tamejiro
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p. 606 - 607
(2008/02/07)
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- Simple palladium(II) precatalyst for suzuki-miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners
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trans-PdBr(N-Succ)(PPh3)2 (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also demonstrated.
- Burns, Michael J.,Fairlamb, Ian J. S.,Kapdi, Anant R.,Sehnal, Petr,Taylor, Richard J. K.
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p. 5397 - 5400
(2008/09/17)
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- AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE
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The invention relates to aminopyrimidine compounds useful for treating diseases mediated by polo-like kinase 1 (Plk1). The invention also relates to the therapeutic use of such aminopyrimidine compounds and compositions thereof in treating disease states associated with abnormal cell growth and unwanted cell proliferation.
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Page/Page column 79-80
(2010/11/08)
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- An effective bismuth-catalyzed benzylation of arenes and heteroarenes
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A highly efficient Bi(OTf)3-catalyzed benzylation of arenes and heteroarenes has been developed. The mild reaction conditions, high yields, operational simplicity and practicability, broad scope, and remarkably low catalyst loading render this environment friendly process an attractive approach to diarylmethane derivatives. The extension to an intramolecular variant of this procedure provides a valuable route to substituted fluorenes.
- Rueping, Magnus,Nachtsheim, Boris J.,Ieawsuwan, Winai
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p. 1033 - 1037
(2007/10/03)
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- Cooperative Friedel-Crafts catalysis in heterobimetallic regime: Alkylation of aromatics by π-activated alcohols
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The highly active Friedel-Crafts alkylation (FCA) catalyst, [Ir(COD)Cl(SnCl3)(SnCl4)(arene)]+Cl- (1-SnCl4), is easily generated in one-pot from [Ir(COD)Cl]2 or [Ir(COD)(μ-Cl)Cl(SnCl3)]2 (1) and SnCl4. The reaction of arenes, heteroarenes with benzyl, and allyl alcohols is promoted by 1-SnCl4 (1 mol %) with high turnover frequency. Kinetic evidence is presented to establish FCA pattern. From dual-catalyst combination studies varying the transition metal and main group metal partner, the efficiency of the present catalysts is attributed to the electrophilic "IrIII-SnIV" core. Copyright
- Choudhury, Joyanta,Podder, Susmita,Roy, Sujit
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p. 6162 - 6163
(2007/10/03)
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- Suzuki cross-coupling reaction of benzylic halides with arylboronic acids in the presence of a tetraphosphine/palladium catalyst
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The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane-[PdCl(C3H5)]2 system catalyses efficiently the Suzuki cross-coupling reaction of benzylic halides with arylboronic acids. A wide variety of benzylic bromides or chlorides and functionalised arylboronic acids lead selectively to the corresponding diarylmethane adducts in good yields. Furthermore, this catalyst can be used at low loading in many cases.
- Chahen, Ludovic,Doucet, Henri,Santelli, Maurice
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p. 1668 - 1672
(2007/10/03)
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- N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
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Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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Page column 73
(2010/01/30)
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- Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
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Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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- Process for the preparation of methylene compounds and the novel compound 2-(2,4-Dichloro-5-fluorobenzyl)thiophene
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Methylene compounds are preferably prepared by reducing an aluminum halide complex of the formula STR1 in which R1 represents a C6 -C10 -aryl radical which is optionally substituted by 1 to 4 C1 -C4 -alkyl radicals, 1 to 4 fluorine, chlorine and/or bromine atoms, one C1 -C8 -alkoxy group and/or one acetoxy group, or represents a heteroaryl radical which is optionally substituted by one C1 -C4 -alkyl radical and/or one fluorine, chlorine or bromine atom and contains 5 to 10 C atoms and one O or S atom and R2 represents a C1 -C12 -alkyl radical which is optionally substituted by 1 to 5 fluorine, chlorine and/or bromine atoms, independently of R1 represents a radical as defined for R1 and, in the case where R1 =a C6 -C10 -aryl radical which is substituted by 1 to 4 fluorine, chlorine and/or bromine atoms, also represents a furyl or thienyl radical, Y represents fluorine, chlorine or bromine, with an amineborane of the formula STR2 in which R3 represents C1 -C4 -alkyl and R4 represents hydrogen or C1 -C4 -alkyl and/or with sodium borohydride and/or with potassium borohydride. 2-(2,4-Dichloro-5-fluorobenzyl)thiophene is obtainable in this way for the first time.
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- Nickel-catalysed electrochemical coupling of 2- and 3-bromothiophene with alkyl and alkenyl halides
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2- or 3-bromothiophene are efficiently coupled with activated alkyl chlorides (α-chloroesters, α-chloroketones, α-chloronitriles), benzyl chloride or vinyl halides, in a one step electrochemical reaction, using the sacrificial anode process and catalysis by NiBr2-2,2'-bipyridine (bipy).
- Durandetti, Muriel,Perichon, Jacques,Nedelec, Jean-Yves
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p. 8683 - 8686
(2007/10/03)
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- THIENYL-, FURYL- AND PYRROLYL SULFONAMIDES AND DERIVATIVES THEREOF THAT MODULATE THE ACTIVITY OF ENDOTHELIN
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Thienyl-, furyl-and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl) furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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- A general, convenient and highly efficient synthesis of diarylmethanes by copper-catalyzed reaction
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Copper-catalyzed reactions of arylmagnesium derivatives with benzyliodides have been developed for the large scale preparation of diarylmethanes. Various diarylmethanes have been prepared in high yield by this reaction, the amount of homocoupled dimers be
- Ku, Yi-Yin,Patel, Ramesh R.,Sawick, David P.
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p. 1949 - 1952
(2007/10/03)
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- Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides
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The electrochemical reduction of a mixture of aryl halides and activated alkyl halides in DMF in the presence of catalytic amount of NiBr2bipy leads to cross-coupling products in good to high yields. The method applies to the synthesis of α-aryl ketones, α-aryl esters, and allylated compounds from readily available organic halides. Optimization of the process has been obtained by slowly adding the most reactive organic halide (usually the activated alkyl halide) during the electrolysis which is best conducted at 70 °C when aryl bromides are involved.
- Durandetti, Muriel,Nedelec, Jean-Yves,Perichon, Jacques
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p. 1748 - 1755
(2007/10/03)
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- SULFONAMIDES AND DERIVATIVES THEREOF THAT MODULATE THE ACTIVITY OF ENDOTHELIN
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Sulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided. The sulfonamides have formula I: STR1 in which Ar 1 is a 3-or 5-isoxazolyl and Ar. sup.2 is selected from among alkyl, including straight and branched chains, aromatic rings, fused aromatic rings and heterocyclic rings, including 5-membered heterocycles with one, two or more heteroatoms and fused ring analogs thereof and 6-membered rings with one, two or more heteroatoms and fused ring analogs thereof. Ar 2 is preferably thiophenyl, furyl, pyrrolyl, naphthyl, and phenyl. Compounds in which Ar. sup.1 is a 4-halo-substituted isoxazole are more active than the corresponding alkyl-substituted compound and compounds in which Ar 1 is substituted at this position with a higher alkyl tend to exhibit greater affinity for ET B receptors than the corresponding lower alkyl-substituted compound.
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- ALKYLATION OF THIOPHENES AND PREPARATION OF BENZOTHIOPHENES USING MODIFIED MONTMORILLONITE CLAY CATALYSTS
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Regioselective benzylation of thiophene and benzothiophene using benzyl chloride and a ZnCl2-promoted montmorillonite catalysts is described.An improved process for the cyclization of (arylthio)acetaldehyde dialkyl acetals to benzothiophenes using the same catalyst is also documented.
- Clark, Peter D.,Kirk, Andrew,Mesher, Shaun T.,Yee, James G.K.
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p. 441 - 444
(2007/10/02)
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- UREA BASED LIPOXYGENASE INHIBITING COMPOUNDS
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Substituted phenyl, naphthyl, and thienyl N-hydroxy urea compounds form a class of potent inhibitors of 5-and 12-lipoxygenase and are thus useful compounds in the treatment of inflammatory disease states where leukotrienes and other products of lipoxygenase enzyme activity are implicated.
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- NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING-II; GRIGNARD COUPLING OF HETEROCYCLIC COMPOUNDS
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A general, versatile method for alkylation and arylation of haloheterocyclic compounds is reported.In the presence of a catalytic quantity of , where dppp stands for Ph2P(CH2)3PPh2, bromothiophenes, halopyridines, haloquinoline, and haloisoquinolines reacted with alkyl and aryl Grignard reagents at room temperature or at ether refluxing temperature to give the cross-coupling products.The coupling reactions has been applied to the synthesis of isoquinoline alkaloids.Reactivities of 2-thienyl and 2-pyridyl Grignard reagents have also been examined.
- Tamao, K.,Kodama, S.,Nakajima, I.,Kumada, M.,Minato, A.,Suzuki, K.
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p. 3347 - 3354
(2007/10/02)
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- Insecticidal perhaloalkylvinylcyclopropanecarboxylates
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Perhaloalkylvinylcyclopropanecarboxylates having the general formula STR1 are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR1 where R1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
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- Kinetics of Bromination of Certain Substituted Thiophenes in Solution
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The general features of the kinetics of bromination of thiophene and substituted thiophenes have been investigated in dry and 15percent aq. acetic acid (v/v) and the Arrhenius activation energy (Ea) accurately determined for ten thiophene derivatives and interpreted.The mechanism proposed is supported with the detection of a ?-complex between bromine and 2-bromothiophene.
- Kannappan, V.,Nanjan, M. J.,Ganesan, R.
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p. 1183 - 1187
(2007/10/02)
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- BASE CLEAVAGE OF SUBSTITUTED - AND -TRIMETHYLSILANE. STABILIZATION OF CARBANIONIC CENTRES BY 2-THIENYL AND 2-FURYL GROUPS
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Rates of cleavage by NaOMe-MeOH at 25 deg C have been determined for (2-thienyl)2CHSiMe3 and for the compounds Ph(2-thienyl)CHSiMe3 and Ph(2-furyl)CHSiMe3 and some of their derivatives with a substituent in the m- or p-position of the phenyl group or the
- Eaborn, Colin,Pirazzini, Graziella,Seconi, Giancarlo,Ricci, Alfredo
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p. 339 - 346
(2007/10/02)
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