- The first enzyme-promoted addition of nitromethane to imines (aza-Henry reaction)
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Enzyme catalytic promiscuity is the ability of a single enzyme active site to catalyze several chemical transformations, among them those which are different from natural. We have attempted to use this feature of enzymes in the nucleophilic addition of nitromethane to aldimines (the aza-Henry reaction) whose chemically catalyzed version leads to synthetically useful β-nitroamines. We succeded in obtaining for the first time the desired products in the yields up to 81%. The most efficient proved lipase TL (from Pseudomonas stutzeri) and oxynitrilase from Arabidopsis thaliana. However, all the reactions investigated were non-stereoselective.
- Janicki, Ignacy,?y?wa, Piotr,Kie?basiński, Piotr
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Read Online
- Synthesis of 3-(Arylsulfonyl)-3-pyrrolines from Allenyl Sulfonamides by Silver Ion Catalysis
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Treatment of allenyl sulfonamides with catalytic amounts of silver fluoride in acetonitrile at reflux afforded the corresponding 3-sulfonyl-3-pyrrolines in excellent yields by intramolecular hydroamination via a 5-endo-trig cyclization. The starting allenyl sulfonamides were prepared by lithiation of allenic sulfones and trapping with various N-sulfonylimines.
- Tata, Rama Rao,Fu, Chencheng,Kelley, Steven P.,Harmata, Michael
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Read Online
- Synthesis of Enantiopure 6,11-Methylene Lipoxin B4 Methyl Ester
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The synthesis of Lipoxin B4 analogs (LXB4) to gain access to stabilized inflammation resolving compounds is an actual field of research. Focusing on variation and stabilization of the conjugated E,Z,E,E C6–C13 tetraene moiety of natural LXB4, a methylene bridge introduced between C6 and C11 suppresses any Z/E isomerization of the C8–C9 olefin. Intending to enable prospective structure variations in connection with the C1–C5 and C14–C20 fragments, a convergent total synthesis has been developed. Optically active C1–C12 building blocks were build-up from cycloheptatriene 1-carbonester (C6–C11, C21) and glutaryl chloride (C1–C5) using Friedel-Crafts-type acylation and chiral HPLC. The C13–C20 segment had been generated via a five-step sequence starting from heptanoyl chloride. Horner key olefination enabled the assembly of the carbon backbone. A final five-step sequence including a chelate Cram reduction of the unsaturated ketone moiety afforded the target 6,11-methylene LXB4 methyl ester.
- Trippe, Lukas,Nava, Analuisa,Frank, Andrea,Nubbemeyer, Udo
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supporting information
p. 1156 - 1167
(2021/02/03)
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- Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
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A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
- Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 2619 - 2624
(2021/04/05)
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- Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines
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A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated azomethine ylides induced by the chiral catalyst. A range of amino acyloxyenamides are delivered in moderate to good yields with good ee values. In addition, a possible catalytic cycle with a transition model is proposed to elucidate the reaction mechanism.
- Li, Xiangqiang,Zeng, Hongkun,Lin, Lili,Feng, Xiaoming
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supporting information
p. 2954 - 2958
(2021/05/05)
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- TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines
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We developed an efficient method for synthesis of tetrafunctionalized 2-imidazolines using TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles. This is the first report of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Br?nsted acid and the reaction worked well over wide scope of substrates in good to excellent yields under mild conditions. The method has the potential to be applied to pharmaceutical design and synthesis of tetrafunctionalized 2-imidazolines.
- Zuo, Qinglu,Shi, Zhichao,Zhan, Feng,Wang, Zhe,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
(2020/01/13)
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- Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines
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A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in
- Wang, Jian,Yi, Wen-Jing
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- Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
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A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.
- Soliman, Hanan A.,El-Shahat, Mahmoud,Soliman, Abdel-Ghany
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p. 584 - 591
(2019/07/31)
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- Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines
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An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.
- Martzel, Thomas,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Brière, Jean-Fran?ois,Perrio, Stéphane
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supporting information
p. 5069 - 5073
(2018/09/14)
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- Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines
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A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.
- Shikora, Jonathan M.,Chemler, Sherry R.
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supporting information
p. 2133 - 2137
(2018/04/30)
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- Visible-Light-Mediated Decarboxylative Benzylation of Imines with Arylacetic Acids
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A straightforward method for the visible-light-mediated decarboxylative benzylation of imines is reported. The key feature of this method is the use of simple primary, secondary, and tertiary arylacetic acids as precursors of benzyl radicals, enabling the facile benzylation of a variety of imines under mild conditions. A variety of structurally diverse β-arylethylamines (37 examples) was accessed using this method.
- Guo, Jing,Wu, Qiao-Lei,Xie, Ying,Weng, Jiang,Lu, Gui
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p. 12559 - 12567
(2018/10/20)
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- Nickel-catalyzed product-controllable amidation and imidation of sp3 C-H bonds in substituted toluenes with sulfonamides
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A nickel-catalyzed product-controllable imidation and amidation of sp3 C-H bonds in substituted toluenes with sulfonamides were developed. Based on the change of the reaction time and atmosphere from N2 to O2, this reaction proceeded in high yields and excellent selectivity under different conditions. Mechanistic details were also described.
- Li, Ze-lin,Jin, Li-kun,Cai, Chun
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supporting information
p. 1317 - 1320
(2017/02/15)
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- Stereoselective Synthesis of a Highly Oxygenated δ-Lactone Related to the Core Structure of (-)-Enterocin
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The title compound was prepared in a concise route starting from an appropriately protected (S)-glyceraldehyde. A highly diastereoselective (d.r. >95:5) Mukaiyama aldol reaction of an acetoacetate-derived silyl enol ether served as the initial step of the synthetic sequence. It was found that protection of the glyceraldehyde as a butane-2,3-dione acetal is required to achieve the desired diastereoselectivity. Upon lactonization, a Tsuji-Trost allylation and a subsequent one-pot reaction cascade including an ozonolysis and an α-hydroxylation gave diastereoselective access to the desired α-hydroxy-β-oxo-δ-lactone. Alternative synthetic approaches are discussed and proof for the configuration of the product is presented.
- Wegmann, Marcus,Bach, Thorsten
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supporting information
p. 209 - 217
(2016/12/24)
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- Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation
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A nitroxyl-radical-catalyzed oxidative coupling reaction between amines with an N-protecting electron-withdrawing group (EWG) and silylated nucleophiles was developed to furnish coupling products in high yields, thus opening up new frontiers in organocatalyzed reactions. This reaction proceeded through the activation of N-halogenated amides by a nitroxyl-radical catalyst, followed by carbon–carbon coupling with silylated nucleophiles. Studies of the reaction mechanism indicated that the nitroxyl radical activates N-halogenated amides, which are generated from N-EWG-protected amides and a halogenation reagent, to give the corresponding imines.
- Moriyama, Katsuhiko,Kuramochi, Masako,Fujii, Kozo,Morita, Tsuyoshi,Togo, Hideo
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p. 14546 - 14551
(2016/11/23)
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- Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes
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A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.
- Kra?em, Jamil,Ghedira, Donia,Ollevier, Thierry
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supporting information
p. 4859 - 4864
(2016/10/12)
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- Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
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An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.
- Fan, Xiaohui,Zhu, Hong-Bo,Lv, Hao,Guo, Kun,Guan, Yong-Hong,Cui, Xiao-Meng,An, Bin,Pu, Yan-Ling
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p. 588 - 592
(2015/09/01)
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- Solvent free acid catalysed direct N-alkylation of amines with alcohols using Al grafted MCM-41
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The catalytic activity of Al grafted MCM-41 (Al-MS) was explored for solvent free acid catalysed direct N-alkylation of amines using alcohols as green alkylating agent to establish a clean method for synthesis of N-alkylated amines. The study revealed that acidity of Al-MS catalyst, reaction conditions and substrate's (amines and alcohols) nature are important factors influencing the N-alkylation reaction. The Al grafted MCM-41 with Si/Al molar ratio of 5 showed excellent activity for N-alkylation of amines with alcohols. The reusability of spent catalyst regenerated by simple washing with acetone was demonstrated for subsequent four reaction cycles.
- Tayade, Kamlesh N.,Mishra, Manish,Munusamy,Somani, Rajesh S.
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- Iron(iii)-salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles
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Chiral iron(iii)-salan complexes catalysed highly enantioselective α-fluorination and α-hydroxylation of β-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions. This journal is the Partner Organisations 2014.
- Gu, Xin,Zhang, Yan,Xu, Zhen-Jiang,Che, Chi-Ming
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supporting information
p. 7870 - 7873
(2014/07/08)
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- Green and scalable aldehyde-catalyzed transition metal-free dehydrative N-alkylation of amides and amines with alcohols
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In contrast to the borrowing hydrogen-type N-alkylation reactions, in which alcohols were activated by transition metal-catalyzed anaerobic dehydrogenation, the addition of external aldehydes was accidentally found to be a simple and effective protocol for alcohol activation. This interesting finding subsequently led to an efficient and green, practical and scalable aldehyde-catalyzed transition metal-free dehydrative N-alkylation method for a variety of amides, amines, and alcohols. Mechanistic studies revealed that this reaction most possibly proceeds via a simple but interesting transition metal-free relay race mechanism. Copyright
- Xu, Qing,Li, Qiang,Zhu, Xiaogang,Chen, Jianhui
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- Hydrocyanation of sulfonylimines using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
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An efficient and eco-friendly method for hydrocyanation of sulfonylimines via one-pot two-step procedure using potassium hexacyanoferrate(II) as a cyanide source, benzoyl chloride as a promoter, and potassium carbonate as a base is described. This protocol has the features of using nontoxic, nonvolatile and inexpensive cyanide source, high yield, and simple work-up procedure.
- Li, Zheng,Li, Rongzhi,Zheng, Huanhuan,Wen, Fei,Li, Hongbo,Yin, Junjun,Yang, Jingya
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p. 1739 - 1743
(2014/01/06)
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- Oxidative imination of toluenes catalyzed by Pd-Au/silica gel under mild reaction conditions
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A Pd-Au/SiO2 catalyst was prepared for the oxidative imination of toluenes with up to 99% yields in the absence of dehydrating agents under mild conditions. Nanoparticles with a PdO layer and PdO-Au core may be the active structure for the reaction.
- Cui, Xinjiang,Shi, Feng,Deng, Youquan
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supporting information; experimental part
p. 7586 - 7588
(2012/10/07)
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- Synthesis of N-sulfonylimines using CeCl3 under neutral conditions
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An efficient and environmentally benign method for the synthesis of N-sulfonylimines is reported. Condensation of aryl sulfonamides with different aromatic aldehydes and ketones gave N-sulfonylimines in good to excellent yields in the presence of 10 mol% CeCl3 as catalyst. This method can be used with both aldehydes and ketones.
- Zhu, Xun,Wei, Yunyang
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experimental part
p. 363 - 364
(2012/09/22)
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- Discovery and mechanistic studies of a general air-promoted metal-catalyzed aerobic n- alkylation reaction of amides and amines with alcohols
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The thermodynamically unfavorable anaerobic dehydrogenative alcohol activation to aldehydes and hydridometal species is found to be the bottleneck in metal-catalyzed N-alkylations due to a general and unnoticed catalyst deactivation by amines/amides. Thus, different from the anaerobic dehydrogenation process in borrowing hydrogen or hydrogen autotransfer reactions that require noble metal complexes or addition of capricious ligands for catalyst activation, the water-producing, exothermic, metal-catalyzed aerobic alcohol oxidation is thermodynamically more favorable and the most effective and advantageous aldehyde generation protocol. This leads to a general and advantageous air-promoted metal-catalyzed aerobic N-alkylation methodology that effectively uses many simpler, less expensive, more available, and ligand-free metal catalysts that were inactive under typical anaerobic borrowing hydrogen conditions, avoiding the use of preformed metal complexes and activating ligands and the exclusive requirement of inert atmosphere protection. This aerobic method is quite general in substrate scope and tolerates various amides, amines, and alcohols, revealing its potentially broad utilities and interests in academy and industry. In contrast to the commonly accepted borrowing hydrogen mechanism, based on a thorough mechanistic study and supported by the related literature background, a new mechanism analogous to the relay race game that has never been proposed in metal-catalyzed N-alkylation reactions is presented.
- Liu, Chuanzhi,Liao, Shiheng,Li, Qiang,Feng, Sunlin,Sun, Qing,Yu, Xiaochun,Xu, Qing
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p. 5759 - 5773
(2011/09/16)
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- Rhodium-catalyzed aerobic N-alkylation of sulfonamides with alcohols
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By using the famous Wilkinson's catalyst, N-alkylation of sulfonamides can be easily realized under mild aerobic conditions by using alcohols as the alkylating reagent, giving monoalkylated sulfonamides in high yields and selectivities with water produced as the only byproduct. This advantageous aerobic method is potentially general in substrate scope that it can also be applied to other amides, amines and alcohols.
- Feng, Sun Lin,Liu, Chuan Zhi,Li, Qiang,Yu, Xiao Chun,Xu, Qing
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scheme or table
p. 1021 - 1024
(2012/06/01)
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- Original synthesis of 2-substituted-4,11-dimethoxy-1-(phenylsulfonyl)-2,3- dihydro-1H-naphtho[2,3-f]indole-5,10-diones using TDAE and Cu-catalyzed reaction strategy
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We report herein an original and rapid synthesis of 2-substituted-4,11- dimethoxy-1-(phenylsulfonyl)-2,3-dihydro-1H-naphtho[2,3-f]indole-5,10-diones by TDAE mediated synthesis of N-benzylsulfonamides followed by an intramolecular N-arylation using Cu-catalyzed system.
- Khoumeri, Omar,Giuglio-Tonolo, Gamal,Crozet, Maxime D.,Terme, Thierry,Vanelle, Patrice
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scheme or table
p. 6173 - 6180
(2011/09/19)
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- Dinuclear zinc catalyzed asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines
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The asymmetric Friedel-Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85-98%) with moderate to high enantiomeric ratios (from 70:30 up to 95:5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl methanamines, which avoids the formation of the undesirable bis- and tris(indolyl)methanes (BIMs and TIMs) byproduct.
- Wang, Bei-Lei,Li, Nai-Kai,Zhang, Jin-Xin,Liu, Guo-Gui,Liu, Teng,Shen, Qi,Wang, Xing-Wang
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supporting information; experimental part
p. 2614 - 2617
(2011/05/08)
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- High-throughput-screening-based identification and structure-activity relationship characterization defined (S)-2-(1-aminoisobutyl)-1-(3-chlorobenzyl) benzimidazole as a highly antimycotic agent nontoxic to cell lines
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Novel nontoxic (S)-2-aminoalkylbenzimidazole derivatives were found to be effective against Candida spp. at low micromolar concentrations using high-throughput screening with infected HeLa cells. A collection of analogues defined the chemical groups relevant for activity. The most active compound was characterized by transcriptional analysis of the response of C. albicans Sc5314. (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole had a strong impact on membrane biosynthesis. Testing different clinically relevant pathogenic fungi showed the selectivity of the antimycotic activity against Candida species.
- Bauer, J?rg,Kinast, Stephan,Burger-Kentischer, Anke,Finkelmeier, Doris,Kleymann, Gerald,Rayyan, Walid Abu,Schr?ppel, Klaus,Singh, Anurag,Jung, Günther,Wiesmüller, Karl-Heinz,Rupp, Steffen,Eickhoff, Holger
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supporting information; experimental part
p. 6993 - 6997
(2011/12/04)
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- Base-promoted selective β-fragmentation of homoallylamines
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A selective β-fragmentation of homoallylamines with the combination of iodobenzene diacetate, iodine, and sodium acetate is reported. The desired carbon-carbon bond cleavage proceeded via a radical β-scission pathway under mild conditions with good functional group tolerance.
- Li, Weixun,Gan, Jianhong,Fan, Renhua
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experimental part
p. 4275 - 4277
(2010/09/07)
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- Highly efficient and diastereoselective synthesis of 1,3-oxazolidines featuring a palladium-catalyzed cyclization reaction of 2-butene-1,4-diol derivatives and imines
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A palladium-catalyzed protocol for effective synthesis of 1,3-oxazolidines has been reported. This method is featured by the high diastereoselectivity (dr up to >98/2) and using the readily available 2-butene-1,4-diol derivatives and imines as substrates.
- Chen, Dongxu,Chen, Xiaoyi,Du, Taiping,Kong, Lichun,Zhen, Renwei,Zhen, Shaocheng,Wen, Yihang,Zhu, Gangguo
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supporting information; experimental part
p. 5131 - 5133
(2010/11/18)
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- Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide
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The Mannich-type reaction between alkyl, aryl and heterocyclic aldimines and sulfonium salts for the synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide (NAP-MgO) is described. These products are obtained in moderate to high yields with moderate diastereoselectivities. The configuration of ethyl-3-{[(4-methylphenyl)sulfonyl] amino}-2-(methylsulfanyl)-3-(4-nitrophenyl)propanoate (major isomer) has been confirmed by X-ray diffraction technique to be anti, and consistent with the assignment based on 1H NMR spectroscopy. These α-sulfanyl- β-amino acid derivatives are important building blocks for pharmaceuticals with potent biological activity.
- Kantam, M. Lakshmi,Mahendar, Koosam,Sreedhar, Bojja,Choudary, Boyapati. M.,Bhargava, Suresh K.,Priver, Steven H.
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experimental part
p. 5042 - 5052
(2010/08/20)
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- Synthesis of oxazoles from α,β-unsaturated carbonyl compounds through 2-acylaziridines
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Oxidative addition of N-aminophthalimide to benzylideneacetone and chalcones followed by thermolysis of the arising 2-aryl-3-acyl-1- phthalimidoaziridines led to the formation of 2,5-disubstituted oxazoles in an overall yield 30-55%. Electron-donor substi
- Beletskii,Kuznetsov
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experimental part
p. 1229 - 1240
(2009/12/09)
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- N-OXIDE-CONTAINING PHARMACEUTICAL COMPOUNDS
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The invention provides a method of preparing a therapeutically active compound having reduced hERG activity, which method comprises: (a) selecting a non-N-oxide drug compound containing a basic tertiary amino group, wherein said non-N-oxide compound is known to have or is suspected of having a therapeutically unacceptable level of hERG inhibitory activity; (b) testing the non-N-oxide drug compound for hERG inhibitory activity; (c) reacting the non-N-oxide drug compound with an oxidising agent to form an N- oxide drug compound having an N-oxide at the basic tertiary amino group; (d) testing the N-oxide drug compound for hERG inhibitory activity; (e) testing the N-oxide drug compound for therapeutically useful activity; (f) comparing the hERG inhibitory activity of the N-oxide drug compound and non- N-oxide drug compound; and (g) when the N-oxide drug compound has therapeutically useful activity and has hERG activity which is at least ten fold less than the hERG inhibitory activity of the non-N-oxide drug compound, formulating the N-oxide drug compound for use in medicine. Also provided by the invention are novel compounds prepared by the aforementioned method and the use of the novel compounds in medicine.
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Page/Page column 40
(2009/01/20)
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- Preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes using magnesium oxide as a heterogeneous and reusable catalyst under solvent-free conditions
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An efficient solvent-free procedure for the preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes in the presence of a catalytic amount of magnesium oxide and tetrabutylammonium bromide (TBAB) under microwave irradiation is described. The advantages of this method are good to high yields, short reaction times, low cost, and matching with green chemistry protocols. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Zare, Abdolkarim,Zare, Ahmad Reza Moosavi,Parhami, Abolfath,Sharghi, Hashem,Khalafi-Nezhad, Ali
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experimental part
p. 2769 - 2776
(2009/09/06)
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- Fragmentation of nitrone triflates to 9-membered rings
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A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.
- Murphy, John A.,Mahesh, Mohan,McPheators, Gary,Vijaya Anand,McGuire, Thomas M.,Carlinga, Robert,Kennedy, Alan R.
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p. 3233 - 3236
(2008/02/11)
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- A novel method for the synthesis of N-sulfonylaldimines by ZnO as a recyclable neutral catalyst under solvent-free conditions
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ZnO acts as an effective catalyst for the rapid synthesis of a range of N-sulfonylaldimines from aromatic aldehydes and sulfonamides under solvent free conditions. The ZnO powder can be reused up to three times after simple washing with distilled water and ethyl acetate.
- Hosseini-Sarvari, Mona,Sharghi, Hashem
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p. 2125 - 2130
(2008/02/08)
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- N-OXIDES OF DIARYLUREA DERIVATIVES AND THEIR USE AS CHK1 INHIBITORS FOR THE TREATMENT OF CANCER
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The invention provides a Chk-1 kinase inhibiting compound of the formula (I) or a salt, solvate or tautomer thereof, wherein: G is CH2, O, NH, NHCO or CONH; A is a group (CH2)n where n is 1 to 4 provided that when G is O or NH, n is at least 2; X1 is nitrogen or CH; X2 is nitrogen or a group CR5; X3 is nitrogen or a group CR5; X4 is nitrogen or CH; provided that no more than two of X2, X3 and X4 are nitrogen; and R1; R2; R3; R4;R5 and R6 are as defined in the claims.
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Page/Page column 51
(2008/06/13)
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- A convenient and efficient method for the preparation of N-sulfonyl aldimines from aromatic aldehydes under solvent-free conditions
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Condensation of a variety of aromatic aldehydes with sulfonamides in the presence of silica chloride by heating afforded novel functionally varied aromatic N-sulfonyl aldimines in good to excellent yields. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Sharghi, Hashem
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p. 873 - 880
(2007/10/03)
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- Efficient and convenient procedure for preparation of N-sulfonylimines catalyzed by montmorillonite K-10
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A general and practical chemical route to the synthesis of N-sulfonylimines using montmorillonite K-10 as the catalyst is described. This method provides several advantages such as operational simplicity, short reaction time, using of inexpensive materials, noncorrosivity, lack of pollution, and high yields. Copyright Taylor & Francis Group, LLC.
- Jin, Tong-Shou,Yu, Mi-Jun,Liu, Li-Bin,Zhao, Ying,Li, Tong-Shuang
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p. 2339 - 2344
(2007/10/03)
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- PROCESS FOR THE PREPARATION OF 21-HYDROXY STEROIDS WITH CONTROL OF THE EPIMERIC DISTRIBUTION AT THE C-21 POSITION
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A process is described for preparing, exclusively by chemical way, 21-hydroxy steroids having progestinic activity, said process having a high stereochemical control at C-21 position.
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Page/Page column 6-7
(2008/06/13)
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- A Solvent-Free Procedure for Synthesis of N-Sulfonylimines Using Microwave Irradiation Catalyzed by ZrO2/S2O2- 8 Solid Superacid
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A solvent-free synthesis of N-sulfonylimines from aldehydes with sulfonamides is described using ZrO2/S2O2- 8 as catalyst under microwave irradiation. This method is fast and high yielding for a range of substrates.
- Jin, Tongshou,Feng, Guoliang,Yang, Mina,Li, Tongshuang
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p. 1277 - 1283
(2007/10/03)
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- A stereoselective synthesis of alkynylaziridines
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Reactions between allenylzinc carbenoid 1 and various imines were examined; trans-substituted alkynylaziridines were produced with excellent diastereoselectivity. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Chemla, Fabrice,Ferreira, Franck,Hebbe, Virginie,Stercklen, Eric
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p. 1385 - 1391
(2007/10/03)
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- Solvent-free synthesis of N-sulfonylimines using microwave irradiation
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N-Sulfonylimines are prepared expeditiously in a one-pot solventless operation by microwave thermolysis of aldehydes and sulfonamides in the presence of benign reagents, calcium carbonate and montmorillonite K 10 clay.
- Vass, Andras,Dudas, Jozsef,Varma, Rajender S.
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p. 4951 - 4954
(2007/10/03)
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- HAMMETT INVESTIGATION OF IODIDE-ION-INDUCED DEOXYGENATIVE REDUCTION OF 2-ARYL'SULPHONYL-3 ARYLOXAZIRIDINES IN METHANOL-WATER (50percent v/v)
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The Hammett substituent dependence of the iodide ion induced deoxygenation of 2-aryl'sulphonyl-3-aryloxaziridines, in aqu. methanol suggests that the reaction proceeds by nucleophilic attack on oxygen with concomitant O-N bond breakage.
- Knipe, A. C.,McAuley, I. E.,Khandelwal, Y.,Kansal, V. K.
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p. 1411 - 1414
(2007/10/02)
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- N,N'-DIACYLSELENIUM AND N,N'-DIACYLSULFUR DIIMIDES
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In the reaction of N,N'-diphenylsulfonylselenium diimide (C6H5SO2N=)2Se with aldehydes, dimethyl sulfoxide, diphenyl selenone, diphenyl selenoxide, triphenylphosphine oxide, etc. the oxygen atom in the E=O group is substituted by a phenylsulfonylimino group.In the reaction of triphenylphosphine with N,N'-diphenylsulfonylselenium diimide N,N'-diphenylsulfonyl-N-triphenylphosphoniohydrazinate is formed.In the reaction of triphenylphosphine with N,N-diacylselenium or N,N'-diacylsulfur sulfimides (CH3CON=)2Se, (C6H5CON=)2Se or (C6H5CON=)2S triphenylphosphine oxide, the corresponding nitrile, and selenium or sulfur are obtained.
- Derkach, N. Ya.,Barashenkov, G. G.,Slyusarenko, E. I.
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- Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
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A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
- Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
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p. 2000 - 2005
(2007/10/02)
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