- Nitration of deactivated aromatic compounds via mechanochemical reaction
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A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.
- Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
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supporting information
(2021/05/05)
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- Novel method for preparing 3-iodo-2-bromotoluene
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The invention discloses a novel method for preparing 2-bromo-3-iodotoluene, and belongs to the field of chemical synthesis. The method specifically comprises the following steps: a, reacting 2-amino-3-nitrotoluene serving as a raw material with a hydrobro
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Paragraph 0030-0032
(2021/08/07)
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- Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions
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Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.
- Fu, Zhengjiang,Jiang, Ligao,Zuo, Qianming,Li, Zhaojie,Liu, Yanzhu,Wei, Zhenhong,Cai, Hu
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supporting information
p. 5416 - 5421
(2018/08/12)
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- Synthetic method of aryl halide taking aryl carboxylic acid as raw material
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A synthetic method of an aryl halide taking aryl carboxylic acid as a raw material is characterized in that a corresponding aryl halide is formed by carrying out substitution reaction on an aryl carboxylic acid compound and haloid salt MX in an organic solvent under the condition that oxygen, a silver catalyst, a copper additive and a bidentate nitrogen ligand exist, wherein M in MX represents alkali metal or alkaline earth metal, and X represents F, Cl, Br or I. Compared with a conventional aryl halide synthetic method, the synthetic method disclosed by the invention has the obvious advantages that reaction raw materials (comprising aryl carboxylic acid and MX) are cheap and easy to obtain, the using amount of a metal catalyst is small, pollution to the environment when the oxygen is used as an oxidant is the smallest, good tolerance to various functional groups on an aromatic ring is obtained, the yield is high, and the like. The synthetic method disclosed by the invention can be widely applied to synthesis in the fields of medicine, materials, natural products and the like in industry and academia.
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Paragraph 0118
(2018/01/03)
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- Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions
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Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.
- Fu, Zhengjiang,Li, Zhaojie,Song, Yuanyuan,Yang, Ruchun,Liu, Yanzhu,Cai, Hu
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p. 2794 - 2803
(2016/04/26)
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- Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones
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Unexpected Smiles! An unusual and highly regioselective synthesis of dibenzoxazepinones by a domino sequence assisted by an unexpected Smiles rearrangement is reported. The process is effective on electronically differentiated phenols and shows a high tolerance to variation in the benzamide substituents. A plausible path for the reaction, supported by preliminary mechanistic data, is offered. Copyright
- Kitching, Matthew O.,Hurst, Timothy E.,Snieckus, Victor
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supporting information; experimental part
p. 2925 - 2929
(2012/05/04)
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- Synthesis and structure-activity relationships of novel benzoxaboroles as a new class of antimalarial agents
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A series of boron-containing benzoxaborole compounds was designed and synthesized for a structure-activity relationship investigation surrounding 7-(HOOCCH2CH2)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1) with the goal of discovering
- Zhang, Yong-Kang,Plattner, Jacob J.,Freund, Yvonne R.,Easom, Eric E.,Zhou, Yasheen,Gut, Jiri,Rosenthal, Philip J.,Waterson, David,Gamo, Francisco-Javier,Angulo-Barturen, Inigo,Ge, Min,Li, Zhiya,Li, Lingchao,Jian, Yong,Cui, Han,Wang, Hailong,Yang, Jian
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experimental part
p. 644 - 651
(2011/03/18)
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- BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
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This invention provides novel compounds of the following formula useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.
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Page/Page column 97
(2011/04/13)
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- Synthesis and SAR of acyclic HCV NS3 protease inhibitors with novel P4-benzoxaborole moieties
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We have synthesized and evaluated a new series of acyclic P4-benzoxaborole-based HCV NS3 protease inhibitors. Structure-activity relationships were investigated, leading to the identification of compounds 5g and 17 with low nanomolar potency in the enzymatic and cell-based replicon assay. The linker-truncated compound 5j was found to exhibit improved absorption and oral bioavailability in rats, suggesting that further reduction of molecular weight and polar surface area could result in improved drug-like properties of this novel series.
- Li, Xianfeng,Zhang, Suoming,Zhang, Yong-Kang,Liu, Yang,Ding, Charles Z.,Zhou, Yasheen,Plattner, Jacob J.,Baker, Stephen J.,Bu, Wei,Liu, Liang,Kazmierski, Wieslaw M.,Duan, Maosheng,Grimes, Richard M.,Wright, Lois L.,Smith, Gary K.,Jarvest, Richard L.,Ji, Jing-Jing,Cooper, Joel P.,Tallant, Matthew D.,Crosby, Renae M.,Creech, Katrina,Ni, Zhi-Jie,Zou, Wuxin,Wright, Jon
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supporting information; experimental part
p. 2048 - 2054
(2011/04/24)
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- Design of living ring-opening alkyne metathesis
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It's alive: A ring-strained alkyne based on dibenzo[a,e][8]annulene undergoes ringopening metathesis polymerization (ROMP) to give a high-molecular-weight poly(ortho-phenylene) featuring alternating ethyl and ethynyl linkers along the polymer backbone. The molybdenumalkylidyne- based catalyst system discriminates between strained and unstrained alkynes to yield a living polymer with an unparalleled low polydispersity.
- Fischer, Felix R.,Nuckolls, Colin
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supporting information; experimental part
p. 7257 - 7260
(2010/11/05)
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- New 2,2′-substituted 6,6′-dimethylbiphenyl derivatives inducing strong helical twisting power in liquid crystals
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New optically active tetra-ortho-substituted biphenyl chiral dopants for nematic liquid crystals are described. It was shown, with respect to our previous results, that biphenyl chiral dopants bearing only mesogenic residues on their 2,2′-positions and wi
- Holzwarth, Richard,Bartsch, Richard,Cherkaoui, Zoubair,Solladie, Guy
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p. 3536 - 3541
(2007/10/03)
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- Palladium-Catalyzed Coupling of 2-Bromoanilines with Vinylstannanes. A Regiocontrolled Synthesis of Substituted Indoles
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The palladium-catalyzed cross-coupling reaction of aryl halides and triflates with vinylstannane reagents has been used to produce a variety of substituted indoles.The mild reaction conditions and selectivity inherent in the coupling reaction have been utilized to produce regiochemically pure 4-, 5-, and 6-substituted indoles.
- Krolski, Michael E.,Renaldo, Alfred F.,Rudisill, Duane E.,Stille, J. K.
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p. 1170 - 1176
(2007/10/02)
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- Insecticidal (1,1'-biphenyl)-3-ylmethyl esters
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[1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
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- Insecticidal [1,1'-biphenyl]-3-ylmethyl esters
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[1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
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- 3-(Pyrrol-1-yl)phenylmethyl esters and intermediates
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3-(Pyrrol-1-yl)phenylmethyl esters and intermediates having the general formula STR1 the use of the esters as pesticides, compositions thereof and a process for preparation are disclosed and exemplified.
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- Electrophilic aromatic substitution. Part 24. The nitration of isopropylbenzene, 2- and 4-isopropyltoluene, 1-chloro-4-isopropylbenzene, 4-isopropylanisole, and 2-bromotoluene: Nitrodeisopropylation
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The kinetics and products of nitration in aqueous sulphuric acid of the title compounds have been studied. 4-Isopropyl-phenol and -anisole are nitrated at or near the encounter rate. In 65-79% H2SO4 2-isopropyltoluene suffers ca. 25% ipso-attack; the only fate of W iPri (ipso-Wheland intermediate) is nitrodeisopropylation. From 4-isopropyltoluene WiPri is also nitrodeisopropylated, but some 1,2-nitro-migration may occur. From the same compound WiMe may be captured by water, rearrange, or give 4-methylacetophenone; a mechanism is proposed for the formation of the last compound. Nitrodeisopropylation occurs without the assistance of water. With 4-isopropylanisole, demethoxylation and nitrodeisopropylation are consequences of the formation of WiPri. The results are consistent with increasing attack at C-4 with increasing acidity, loss of isopropyl without assistance from water, and decomposition of the unobserved intermediate, 4-isopropyl-4-nitrocyclohexa-2,5-dienone, by two processes. One, acid-catalysed process gives 4-nitrophenol and possibly 4-isopropyl-2-nitrophenol. The other, probably radical, process gives 4-isopropyl-2-nitrophenol. In contrast to 4-bromotoluene, 2-bromotoluene is not nitrodebrominated.
- Manglik, Ajay K.,Moodie, Roy B.,Schofield, Kenneth,Tobin, Geoffrey D.,Coombes, Robert G.,Hadjigeorgiou, Panicos
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p. 1606 - 1616
(2007/10/02)
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