- Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant
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This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.
- Fernandes, Rodney A.,Kumar, Praveen,Yadav, Sandhya S.
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p. 427 - 443
(2022/01/20)
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- Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides
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This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source andN-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.
- Chen, Qing-Yun,Guo, Yong,Hu, Xiaojun,Liu, Chao,Liu, Yongan,Ma, Xiaoyu,Pan, Qijun,Pang, Wan,Wu, Jingjing
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supporting information
p. 8999 - 9003
(2021/11/04)
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- An efficient approach to 3-thioether-functionalized 2,3-dihydrobenzofurans via a metal-free intramolecular radical cyclization/thiolation cascade reaction
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A diverse series of 3-thioether-functionalized 2,3-dihydrobenzofurans were prepared by an intramolecular radical cyclization/thiolation cascade reaction of alkenyl-tethered arenediazonium salts with thiophenols under transition-metal-free conditions. The
- Chen, Tingting,Zheng, Renhua,Yu, Jingmiao
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supporting information
p. 2204 - 2212
(2021/05/29)
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- Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
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The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
- Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
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supporting information
(2020/05/18)
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- Base-mediated intramolecular one-pot double-cyclization of epoxide-tethered 2-fluorobenzenesulfonamides: An avenue to 1,4-benzoxazine-fused benzothiaoxazepine-1,1-dioxides
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Herein, we describe the synthesis of hitherto unknown 1,4-benzoxazine-fused benzothiaoxazepine-1,1-dioxides by a NaH-promoted intramolecular one-pot double-cyclization of epoxide-tethered 2-fluorobenzene sulfonamides. Mechanistically, the reactions proceed via an intramolecular epoxide ring-opening followed by an intramolecular nucleophilic aromatic substitution. The high yields, mild conditions, complete regio- and diastereoselectivity, and a wide substrate scope render this protocol well suited for drug discovery efforts.
- Das, Jonali,Borah, Biraj Jyoti,Das, Sajal Kumar
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supporting information
p. 220 - 224
(2020/01/13)
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- Boron-Promoted Ether Interchange Reaction: Synthesis of Alkyl Nitroaromatic Ethers from Methoxynitroarenes
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The first protocol for boron-promoted ether interchange reaction of methoxynitroarenes was described. A series of methoxynitroarenes and alcohols, including primary, secondary, as well as tertiary alcohols were reacted smoothly in moderate to good yields under the optimized reaction conditions. This protocol constitutes an operationally simple and scalable strategy for the synthesis of alkyl nitroaromatic ethers. Moreover, the new reactivity of boron reagents was discovered.
- Liu, Zhenwei,Luan, Nannan,Lu, Hongtao,Liang, Apeng,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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p. 702 - 707
(2020/02/11)
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- Process for synthesizing ramalin not using Tin as a heavy metal
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The present invention relates to a method for synthesizing ramalin. More particularly, the present invention relates to the method for preparing ramalin by conducting a reaction of a glutamic acid derivative manufactured by using alkyl chloroformate with
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Paragraph 0041; 0044-0046
(2019/09/07)
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- Pd-Catalyzed Enantioselective Double Heck Reaction
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An asymmetric Pd-catalyzed intramolecular followed by an intermolecular double Heck reaction of arenediazonium salts with simple alkenes is disclosed. This reaction features mild reaction conditions, simple operation, and excellent functional group tolera
- Ju, Baihang,Chen, Shigui,Kong, Wangqing
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supporting information
p. 9343 - 9347
(2019/12/02)
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- Facile one-pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers under mild conditions
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We report here the facile, room temperature, catalyst free, one pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers. Anhydrous potassium carbonate (K2CO3) as a mild base along with dimethyl sulfoxide gener
- Sakate, Sachin,Kamble, Sumit,Chikate, Rajiv,Rode, Chandrashekhar
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p. 462 - 470
(2017/03/27)
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- Copper-catalyzed carbochlorination or carbobromination via radical cyclization of aryl amines
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A copper-catalyzed radical carbochlorination or carbobromination is reported. Intramolecular cyclization occurred through aryl radicals generated in situ from bench-stable aryl amines with aqueous hydrogen halides as the halogen sources. A variety of (3-h
- Ouyang, Jianing,Su, Xiaolong,Chen, Yu,Yuan, Yaofeng,Li, Yi
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supporting information
p. 1438 - 1441
(2016/03/12)
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- A rapidly photo-activatable light-up fluorescent nucleoside and its application in DNA base variation sensing
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A new DNA building block (dTetU) bearing a tetrazole and allyloxy group at N-phenyl ring linked through an aminopropynyl linker to the 5-position of 2′-deoxyuridine was synthesized. The modified DNA can be lit up via a photoinduced intramolecul
- He, Zhiyong,Chen, Yuqi,Wang, Yafen,Wang, Jiaqi,Mo, Jing,Fu, Boshi,Wang, Zijing,Du, Yuhao,Zhou, Xiang
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supporting information
p. 8545 - 8548
(2016/07/14)
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- Investigation on Claisen rearrangement of allyl phenyl ethers in near-critical water
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Catalyst-free Clasien rearrangement of allyl phenyl ethers were investigated in near-critical water. The effects on the reaction in near-critical water and conventional conditions were compared. The results demonstrate that near-critical water could greatly accelerate the Claisen rearrangement of allyl phenyl ethers. This process is simple, fast, efficient and environmentally benign.
- Xiao, Shangyou,He, Yi,Xu, Guang,Liu, Qi
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p. 3299 - 3305
(2015/06/08)
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- In situ production of silver nanoparticles on an aldehyde-equipped conjugated porous polymer and subsequent heterogeneous reduction of aromatic nitro groups at room temperature
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In a metal-free procedure, chelating thiol groups and an electrophile react to assemble a robust, conjugated porous polymer with pendant aldehyde functionalities. These groups are able to reduce Ag(I) ions to generate, in situ, Ag(0) nanoparticles evenly dispersed in the polymer matrix. The Ag(0)-polymer composite enables selective reduction of aromatic nitro compounds as a heterogeneous catalyst, and can be conveniently recycled multiple times.
- Liu, Jie,Cui, Jieshun,Vilela, Filipe,He, Jun,Zeller, Matthias,Hunter, Allen D.,Xu, Zhengtao
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supporting information
p. 12197 - 12200
(2015/07/27)
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- Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines
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Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5-exo or 6-exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation products. Running the reaction in the presence of PhTeTePh affords the phenyltellurated cyclized products.
- Hartmann, Marcel,Studer, Armido
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supporting information
p. 8180 - 8183
(2014/08/18)
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- A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: Synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols
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Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1a-c. As this takes place, regardless of the reagent used (AD-mix-α or AD-mix-β), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1a-c allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase.
- Bredikhina, Zemfira A.,Kurenkov, Alexey V.,Antonovich, Olga A.,Pashagin, Alexander V.,Bredikhin, Alexander A.
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p. 1015 - 1021
(2014/08/18)
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- Twofold carbon-carbon bond formation by intra- and intermolecular radical reactions of aryl diazonium salts
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Cascade reactions: A variety of novel cascade reactions can be performed when the known and well-studied radical 5- or 6-exo-cyclization of an aryl diazonium salt is conducted in the presence of alkenes and further optional scavengers (see scheme). Copyri
- Jasch, Hannelore,Landais, Yannick,Heinrich, Markus R.
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p. 8411 - 8416
(2013/07/11)
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- 8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones: Dual-acting 5-HT1 receptor antagonists and serotonin reuptake inhibitors-Part II
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8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones have been identified as highly potent 5-HT1A/B/D receptor antagonists with and without additional SerT activity and a high degree of selectivity over hERG potassium channels. Modula
- Bromidge, Steven M.,Bertani, Barbara,Borriello, Manuela,Bozzoli, Andrea,Faedo, Stefania,Gianotti, Massimo,Gordon, Laurie J.,Hill, Matthew,Zucchelli, Valeria,Watson, Jeannette M.,Zonzini, Laura
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scheme or table
p. 2338 - 2342
(2009/12/31)
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- Synthesis and in-vitro biological activity of macrocyclic urea Chk1 inhibitors
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A variety of macrocyclic urea compounds were prepared as potent Chk1 inhibitors by modifying the C5 position of the benzene ring of the macrocyclic urea with ether moieties, aliphatic carbon chains, amide and halides. Enzymatic activity less than 20 nM was observed in 29 of 40 compounds. Compounds 14, 46d, and 48j provided the best overall results in the cellular assays as they abrogated doxorubicin-induced cell cycle arrest (IC50 = 3.31, 3.08, and 3.13 μM) and enhanced doxorubicin cytotoxicity (IC50 = 0.54, 1.27, and 0.96 μM) while displaying no single agent activity, respectively.
- Li, Gaoquan,Tao, Zhi-Fu,Tong, Yunsong,Przytulinska, Magdalena K.,Kovar, Peter,Merta, Philip,Chen, Zehan,Zhang, Haiying,Sowin, Thomas,Rosenberg, Saul H.,Lin, Nan-Horng
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p. 6499 - 6504
(2008/03/18)
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- Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
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A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
- Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
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p. 565 - 567
(2007/10/03)
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- FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS
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Compounds of formula (I) wherein R1, R2, X, A, Y, B, Z1, Q, p, r and s are defined in the specification for treating inter alia psychotic disorders, depressive disorders, anxiety disorders and sexual dysfunctions.
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Page/Page column 41
(2010/10/20)
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- An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans
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Twelve substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-mediated C- and O-allyl isomerization followed by ring-closing metathesis.
- Van Otterlo, Willem A.L.,Morgans, Garreth L.,Madeley, Lee G.,Kuzvidza, Samuel,Moleele, Simon S.,Thornton, Natalie,De Koning, Charles B.
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p. 7746 - 7755
(2007/10/03)
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- Ring-closing metathesis for the synthesis of 2H- and 4H-chromenes
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Six 4H-chromenes were synthesized from substituted phenols using vinylstannylation and ring-closing metathesis (RCM) as key steps. In addition, a different approach involving amongst other steps, an aryl allyl isomerization and RCM afforded a set of seven 2H-chromenes from phenolic precursors.
- Van Otterlo, Willem A.L.,Ngidi, E. Lindani,Kuzvidza, Samuel,Morgans, Garreth L.,Moleele, Simon S.,De Koning, Charles B.
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p. 9996 - 10006
(2007/10/03)
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- DIHYDROBENZOFURANYL ALKANAMINE DERIVATIVES AS 5HT2C AGONISTS
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Compounds of Formula (I) or pharmaceutically acceptable salts thereof are provided: Formula (I) which are agonists or partial agonists of the 2C subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.
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Page/Page column 107
(2008/06/13)
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- Preparation of aryl allyl ether in the recyclable ionic liquid [bmim]PF6
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The recyclable room temperature ionic liquid [bmim]PF6, namely 1-butyl-3-methyl-imidazolium hexafluorophosphate, is used as an alternative solvent to dipolar aprotic solvents for the synthesis of aryl allyl ether by the Williamson method.
- Zhou, Mei-Yun,Li, Yi-Qun
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p. 328 - 328
(2007/10/03)
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- Dihydrobenzoxazines and Tetrahydroquinoxalines by a Tandem Reduction-Reductive Amination Reaction
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A tandem reduction-reductive amination reaction has been applied to the synthesis of 3,4-dihydro-2H-1,4-benzoxazines and 1-acetyl-1,2,3,4-tetrahydroquinoxalines. The nitroketones required for the benzoxazine ring closures were prepared by (A) alkylation of the anion derived from 2-nitrophenol with an allylic halide or (B) nucleophilic aromatic substitution of an allylic alkoxide on 2-fluoro-1-nitrobenzene followed by ozonolysis. Precursors for the quinoxalines were prepared by alkylation of the anion of 2-nitroacetanilide with an allylic halide followed by ozonolysis. Catalytic hydrogenation of the nitroketones using 5% palladium-on-carbon in methanol then gave the target heterocycles by a reduction-reductive amination sequence. The N-methyl derivatives for both ring systems were easily prepared by adding 5-10 equivalents of aqueous formaldehyde prior to the reduction. The dihydrobenzoxazines were isolated in high yield following purification by chromatographic methods; tetrahydroquinoxalines were isolated in a similar manner and possessed differentiated functionality on the two nitrogens.
- Bunce, Richard A.,Herron, Derrick M.,Hale, Lu Y.
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p. 1031 - 1039
(2007/10/03)
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- A new synthesis of substituted 2,5-dihydro[b]-oxepines
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Based on Claisen rearrangement, Baeyer-Villiger oxidation, and ring-closing metathesis (RCM), a series of substituted 2,5-dihydrobenzo[b]-oxepines were synthesized from isovanillin in good over-all yields. Other appropriate substituted 2,5-dihydrobenzo[b]oxepines prepared from corresponding phenol derivatives were also described.
- Wang, Eng-Chi,Hsu, Ming-Kun,Lin, Yu-Li,Huang, Keng-Shiang
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p. 1997 - 2010
(2007/10/03)
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- Preparation of tricyclic and tetracyclic benzoxepin derivatives by one-pot enyne metathesis/Diels-Alder reaction
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Tricyclic and tetracyclic benzoxepin derivatives were prepared by one-pot enyne metathesis/Diels - Alder reactions starting from differently substituted 2-allyl-1-propargyloxybenzenes (endo stereoselectivity).
- Moreno-Ma?as,Pleixats,Santamaria
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p. 1784 - 1786
(2007/10/03)
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- Novel exploration of the SNAr reaction
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Propargylic, allylic and benzylic alcohols prove to be fairly successful as activated nucleophiles, under mild conditions for the SNAr reaction.
- Raeppel, Stéphane,Raeppel, Franck,Suffert, Jean
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p. 794 - 796
(2007/10/03)
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- Tetrathiafulvalene: a catalyst for sequential radical-polar reactions
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The reaction between tetrathiafulvalene (TTF) and suitable arenediazonium salts leads to products arising from an ordered sequence of reactions featuring electron transfer, loss of nitrogen, radical cyclisation and nucleophilic substitution.The tetrathiafulvalenium salt 6 is shown to be an intermediate in the reaction, with substitution of TTF occuring via an SN1 mechanism.The reactions are catalytic in TTF and the final substitution can be achieved by several nucleophiles.Extension of the reaction to the synthesis of bi- and tricyclic ring systems has been investigated.
- Fletcher, Rodney J.,Lampard, Christopher,Murphy, John A.,Lewis, Norman
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p. 623 - 634
(2007/10/02)
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- A SIMPLE AND EFFICIENT METHOD FOR PREPARATION OF ALLYL ARYL ETHERS VIA POLYMER SUPPORTED REAGENTS
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Allyl aryl ethers were synthesized in excellent yields and in a state of high purity by reaction of polymer-supported phenoxide ions with allyl bromide in ethanol at room temperature.
- Salunkhe, M.M.,Thorat, M.T.,Mane, R. B.,Sande, A.R.,Wadgaonkar, P.P.
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p. 691 - 694
(2007/10/02)
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- Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans
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A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.
- Yodo, Mitsuaki,Harada, Hiroshi
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p. 2361 - 2368
(2007/10/02)
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- Miticidal 2-(2-alkyl-2,3-dihydrobenzofuran-7-yl)-N-alkoxy-N-alkyl-diazenecarboxamides
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Miticidal 2-(2-alkyl-4-(or 5)-bromo (or chloro)-2,3-dihydrobenzofuran-7-yl)-N-alkoxy-N-alkyldiazenecarboxamides.
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- Aphicidal 3-(2-alkyl-2,3-dihydrobenzofuran-7-yl)-5-(R,R1 -amino)-1,3,4-oxadiazol-2(3H)-ones
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Certain aphicidal 3-(2-alkyl-2,3-dihydrobenzofuran-7-yl)-5-(R,R1 -amino)-1,3,4-oxadiazol-2(3H)-ones.
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- Kinetics and Mechanism of Reactions of Sodium Phenoxides with Allyl Halides
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Kinetics of reactions of sodium phenoxides with allyl chloride and allyl bromide in aprotic solvent mixtures have been reported.The reactions are overall second order processes.The reaction results in an O-alkylated product.Protic solvents retard the reaction.A mechanism commensurate with the kinetic data has been suggested.
- Panigrahi, G. P.,Sinha, T. K.
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