- Aniline-Tetramic Acids from the Deep-Sea-Derived Fungus Cladosporium sphaerospermum L3P3 Cultured with the HDAC Inhibitor SAHA
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Four new tetramic acids, cladosins H-K (1-4), and a related known compound, cladodionen (5), were isolated from the culture of the Mariana Trench (depth 6562 m) sediment-derived fungus Cladosporium sphaerospermum L3P3 treated with the histone deacetylase
- Zhang, Zhenzhen,He, Xueqian,Wu, Guangwei,Liu, Congcong,Lu, Changjun,Gu, Qianqun,Che, Qian,Zhu, Tianjiao,Zhang, Guojian,Li, Dehai
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Read Online
- Optimization of physicochemical properties is a strategy to improve drug-likeness associated with activity: Novel active and selective compounds against Trypanosoma cruzi
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Trypanosoma cruzi is the causing agent of Chagas disease, a parasitic infection without efficient treatment for chronic patients. Despite the efforts, no new drugs have been approved for this disease in the last 60 years. Molecular modifications based on
- Amaral, Maiara,Romanelli, Maiara M.,Tempone, Andre G.,Varela, Marina T.,de Castro Levatti, Erica V.,Fernandes, Jo?o Paulo S.
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- Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids
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A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.
- Tang, Jing-Jing,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
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p. 13955 - 13961
(2021/11/20)
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- Efficient nitriding reagent and application thereof
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The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0179-0182
(2021/03/31)
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- Visible-light induced one-pot hydrogenation and amidation of nitroaromatics with carboxylic acids over 2D MXene-derived Pt/N-TiO2/Ti3C2
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Pt nanoparticles supported on N doped titanium dioxide/titanium carbide (MXene) heterojunctions were employed as photocatalysts for the tandem reactions between aromatic nitro compounds and carboxylic acids to produce amide products. The 3%Pt/N-TiO2/Ti3C2 heterojunction was prepared by in situ grew TiO2 on Ti3C2 nanosheets and then N doped TiO2 with melamine, Pt nanoparticles with 3.3 nm mean diameter well dispersed on N-TiO2/Ti3C2. 3%Pt/N-TiO2/Ti3C2 had excellent amidation activity and chemoselectivity under visible-light irradiation. The elevated catalytic performance of 3%Pt/N-TiO2/Ti3C2 was owing to the improvement in photogenerated electron and hole separation efficiency through charge short-range directional transmission caused by the intimate contact between the TiO2 and the conductive Ti3C2. This direct hydrogenation along with amidation between nitroaromatics and carboxylic acids own actual merits in the amides produce with no harmful byproducts. In situ DRIFTS spectra verified that the amidation activation with visible light irradiation at 25 °C was much faster than heating.
- Jiang, Heyan,Hu, Zujie,Gan, Chuan,Sun, Bin,Kong, Shuzhen,Bian, Fengxia
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- Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
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A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
- Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
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p. 2820 - 2826
(2021/02/01)
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- Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
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Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.
- Zhu, Mengyi,Wang, Lijuan,He, Jing
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supporting information
p. 2030 - 2035
(2020/11/30)
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- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
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The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
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supporting information
p. 281 - 285
(2020/01/28)
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- Nickel-catalyzed: C-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
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A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamides with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway. This journal is
- Yang, Peng,Wang, Xiuhua,Ma, Yu,Sun, Yaxin,Zhang, Li,Yue, Jieyu,Fu, Kaiyue,Zhou, Jianrong Steve,Tang, Bo
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supporting information
p. 14083 - 14086
(2020/11/20)
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- Method for preparing amide compounds
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The invention discloses a method for preparing amide compounds. The method comprises the step of subjecting organic carboxylate with a structure represented by a formula (I) shown in the description and an amine compound with a structure represented by a formula (II) shown in the description to a grinding reaction, thereby preparing an amide compound with a structure represented by a formula (III)shown in the description and an alcohol compound with a structure represented by a formula (IV) shown in the description. According to the synthesis method, a heat source is not required to supply heat, an organic solvent is not required to serve as a medium, the operation is simple, the reaction time is short, the aftertreatment is simple, and thus, industrial production is easy to achieve.
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Paragraph 0079-0080
(2019/06/05)
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- A method for utilizing the modified mesoporous material catalytic preparation fu linuo his method (by machine translation)
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The invention provides a coupling agent suberic acid bitter wine and modified mesoporous silica coupling/catalytic system for preparing fu linuo his method, the method comprises the following steps: preparation suberic acid bitter wine and coupling agent modified mesoporous silicon dioxide; wherein said hydrophilic modified mesoporous silicon dioxide pre-treatment reactant [...] 1 - 2 h, with aniline or a salt thereof to react to form an intermediate product of bromoxynil aniline acid; in the presence of a modified mesoporous silica obtained bromoxynil aniline acid with hydroxylamine or its salt by the reaction of the fu linuo he. The method of the invention the selectivity and the yield is high, the amidation reaction time is short, the resulting fu linuo he purity as high as 99% or more. (by machine translation)
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Paragraph 0032; 0033; 0036; 0039; 0040
(2019/01/23)
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- Synthetic method of amide compound
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The invention discloses a synthetic method of an amide compound. An organic carboxylic acid compound with the structure of a formula (I) and an amine compound with the structure of a formula (II) aresubjected to a grinding reaction to obtain the amide compound with the structure of a formula (III) in the presence of a coupling reagent. According to the synthetic method, a heat source is not required to be used for heating, and an organic solvent is also not required to be used as a medium, operation is easy, the reaction time is short, post-processing is easy, and industrial production is easy to achieve(Please see the specifications for the formulas).
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Paragraph 0083-0086
(2019/06/08)
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- Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives
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A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.
- Huang, Binbin,Zhao, Yating,Yang, Chao,Gao, Yuan,Xia, Wujiong
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supporting information
p. 3799 - 3802
(2017/07/26)
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- 2-substituted aniline as a simple scaffold for LuxR-regulated QS modulation
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The ability of the 2-substituted aniline motif to serve as a scaffold for designing potential LuxR-regulated quorum sensing (QS) modulators has been investigated, using docking experiments and biological evaluation of a series of 15 specially synthesized compounds. Aniline, 2-acetyl-aniline and 2-nitroaniline were considered, as well as their N-acylated derivatives. Docking experiments showed that the 2-substituted aniline motif fits within the LuxR binding site at the place of the lactone moiety of AHL, and the biological evaluation revealed QS antagonisitic activity for several compounds, validating the hypothesis that this scaffold acts on QS. Structure activity relationships are discussed regarding interactions with the key residues of the LuxR binding site, showing significant variations in the H-bonding pattern.
- Li, Sizhe,Wawrzyniak, Julien,Queneau, Yves,Soulère, Laurent
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- One for Many: A Universal Reagent for Acylation Processes
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This work describes acylation reactions facilitated by a type of heterocycle-based acyl transfer agent, 2-acyloxypyridazinone. Reactions of 2-acyloxypyridazinone with carboxylic acids yield mixed carbonic anhydride intermediates, which are reactive and could be coupled with a wide range of substrates including acids, amines, alcohols, and thiols. The wide substrate scope, ease of operation (no additive or catalyst), storage and handling stability, and atom-efficiency from recycling the heterocycle carrier make the reported acylating agent attractive for acylation-based coupling reactions.
- Moon, Hyun Kyung,Sung, Gi Hyeon,Kim, Bo Ram,Park, Jong Keun,Yoon, Yong-Jin,Yoon, Hyo Jae
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supporting information
p. 1725 - 1730
(2016/06/09)
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- Aerobic oxidative transformation of primary alcohols and amines to amides promoted by a hydroxyapatite-supported gold catalyst in water
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In the presence of an easily prepared hydroxyapatite-supported gold catalyst, namely Au/HAP, various kinds of structurally diverse primary alcohols including benzylic and aliphatic ones, and amines involving aromatic and secondary ones could be converted into the corresponding amides in water with up to 99% yield. Meanwhile, on the basis of experimental observations and literatures, a plausible reaction pathway was described to elucidate the reaction mechanism.
- Wang, Wentao,Cong, Yu,Zhang, Leilei,Huang, Yanqiang,Wang, Xiaodong,Zhang, Tao
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supporting information
p. 124 - 127
(2014/01/06)
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- Aerobic oxidative coupling of alcohols and amines over Au-Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines
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A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au-Pd alloy catalysts (Au-Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.
- Zhang, Leilei,Wang, Wentao,Wang, Aiqin,Cui, Yitao,Yang, Xiaofeng,Huang, Yanqiang,Liu, Xiaoyan,Liu, Wengang,Son, Jin-Young,Oji, Hiroshi,Zhang, Tao
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supporting information
p. 2680 - 2684
(2013/10/08)
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- XtalFluor-E, an efficient coupling reagent for amidation of carboxylic acids
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Amides were produced from carboxylic acids and amines by using XtalFluor-E as an activator. Even poorly reactive carboxylic acids can be transformed to amides. In addition, optically active amines and/or carboxylic acids were not epimerized/racemized during the process.
- Orliac, Aurélie,Gomez Pardo, Domingo,Bombrun, Agnès,Cossy, Janine
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supporting information
p. 902 - 905
(2013/03/29)
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- Synthesis of three novel anionic gemini surfactants and comparative studies of their assemble behavior in the presence of bovine serum albumin
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Three novel anionic sulfonate gemini surfactants, sodium 4,4′-(10,19-dioxo-9,11,18,20-tetraazaoctacosane-9,20-diyl) dibenzenesulfonate (Surfactant I), sodium 4,4′-(12,21-dioxo-11,13,20,22- tetraazadotriacontane-11,22-diyl) dibenzenesulfonate (Surfactant II), and sodium 4,4′-(14,23-dioxo-13,15,22,24-tetraazahezatriacontane-13,24-diyl) dibenzenesulfonate (Surfactant III), with different lengths of hydrophobic tail have been synthesized, and their assembly behavior in the presence of bovine serum albumin (BSA) has been studied using spectral methods and molecular modeling methods at physiological pH and 298 K. Critical micelle concentrations (CMCs) of the three surfactants have been determined by surface tension measurements. Despite the obvious decrease of CMC with the increase of tail length, fluorescence spectra have shown much closer CAC in the presence of BSA. Surfactant II shows the highest CAC of 3.19 × 10-5 mol L -1 compared with the other two. The polarity of the microenvironment in BSA-surfactant systems has been investigated using pyrene as the probe. In addition, far-UV CD spectra studied the change of the secondary structure content of BSA caused by the three surfactants. The features of the assembly behavior were discussed by three concentration regions. Surfactant II could unfold the protein much more efficiently than the other two surfactants at low concentration, but at high concentration, the change of the secondary structure and the formation of hydrophobic microenvironment show a direct relationship to the length of the hydrophobic tail with the increase of the surfactant concentration.
- Ge, Yu-Shu,Tai, Shu-Xin,Xu, Zi-Qiang,Lai, Lu,Tian, Fang-Fang,Li, Dong-Wei,Jiang, Feng-Lei,Liu, Yi,Gao, Zhi-Nong
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scheme or table
p. 5913 - 5920
(2012/07/27)
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- Thermally decomposed Ni-Fe-hydrotalcite: A highly active catalyst for the solvent-free N-acylation of different amines by acid chlorides
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A composite Ni-Fe catalyst obtained from the thermal decomposition of Ni-Fe-hydrotalcite at 600 °C shows very high activity in the solvent-free N-acylation of amines by different acid chlorides with high product yields under very mild reaction conditions (viz. room temperature, short reaction period and small amount of catalyst). The catalyst also shows excellent reusability in the reaction. The crystalline phases present in the catalyst are mixed oxides and hydroxides of nickel and iron. The high catalytic activity of the decomposed Ni-Fe-hydrotalcite is attributed to the formation of uniformly distributed Ni-Fe metal oxides and hydroxides.
- Choudhary,Dumbre
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experimental part
p. 1351 - 1356
(2012/01/06)
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- Nano sulfated titania as solid acid catalyst in direct synthesis of fatty acid amides
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Nanosized sulfated titania was prepared by a sol-gel hydrothermal process. X-ray diffraction (XRD), transmission electron, and scanning electron micrographs (TEM and SEM), FT-IR specific surface area, and BET N2 adsorption were employed to characterize the properties of the synthesized sulfated TiO2. The results indicate that both anatase and rutile TiO2 are obtainable. This prepared sulfated titania showed high catalytic activity in direct amidation of fatty acids as well as benzoic acids with various amines under solvent-free conditions.
- Hosseini-Sarvari, Mona,Sodagar, Esmat,Doroodmand, Mohammad Mahdi
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supporting information; experimental part
p. 2853 - 2859
(2011/05/17)
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- An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine
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A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.
- Luo, Qun-Li,Lv, Lina,Li, Yu,Tan, Jian-Ping,Nan, Wenhui,Hui, Qun
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supporting information; experimental part
p. 6916 - 6922
(2012/01/06)
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- Samarium-mediated mild and facile method for the synthesis of amides
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Samarium-mediated facile method for the formation of amide bonds by the reaction of acyl chlorides and amines is described. The reaction afforded high yields of the desired amides under mild and neutral conditions.
- Shi, Feng,Li, Jian,Li, Chunju,Jia, Xueshun
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experimental part
p. 6049 - 6051
(2010/11/21)
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- Synthesis of amides and lactams in supercritical carbon dioxide
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(Chemical Equation Presented) Supercritical carbon dioxide can be employed as an environmentally friendly alternative to conventional organic solvents for the synthesis of a variety of carboxylic amides. The addition of amines to ketenes generated in situ via the retro-ene reaction of alkynyl ethers provides amides in good yield, in many cases with ethylene or isobutylene as the only byproducts of the reaction. Reactions with ethoxy alkynes are performed at 120-130°C, whereas tert-butoxy derivatives undergo the retro-ene reaction at 90°C. With the exception of primary, unbranched amines, potential side reactions involving addition of the amines to carbon dioxide are not competitive with the desired C-N bond-forming reaction. The amide synthesis is applicable to the preparation of β-hydroxy and β-amino amide derivatives, as well as amides bearing isolated carbon-carbon double bonds. Preliminary experiments aimed at developing an intramolecular variant of this process to afford macrolactams suggest that the application of CO2/co-solvent mixtures may offer advantages for the synthesis of large-ring compounds.
- Mak, Xiao Yin,Ciccolini, Rocco P.,Robinson, Julia M.,Tester, Jefferson W.,Danheiser, Rick L.
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experimental part
p. 9381 - 9387
(2010/03/04)
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- Synthesis of platensimycin analogues and their antibiotic potency
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Platensimycin is a natural product isolated from various strains of Streptomyces platensis which exhibits antimicrobial activity against Gram positive bacteria, including vancomycin- and linezolide-resistant species. Analogues of platensimycin were synthesized from 3-aminobenzoic acid or other aniline derivatives and several alkyl- and aryl-carboxylic acids. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi.
- Krauss, Juergen,Knorr, Veronika,Manhardt, Vera,Scheffels, Stefanie,Bracher, Franz
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experimental part
p. 386 - 392
(2009/04/16)
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- Tighter ion pair effect and scale-up study in microwave assisted aminolysis of enolizable esters using potassium tert-butoxide (t-BuOK)
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The tighter ion pair effect and scale-up study in aminolysis of enolizable esters using potassium tert-butoxide (t-BuOK) under microwave irradiations is described. This method provides synthetic advantages in terms of reaction time, product yields, eco-friendly environment and scale-up feasibility over the conventional heating method.
- Polshettiwar, Vivek,Kaushik
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p. 773 - 777
(2007/10/03)
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- Compounds with activity on muscarinic receptors
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Compounds and methods are provided for the alleviation or treatment of diseases or conditions in which modification of muscarinic m1 receptor activity has a beneficial effect. In the method, a therapeutically effective amount of a selective muscarinic m1
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- Selective Activation of Primary Carboxylic Acids by Electron-rich Triarylbismuthanes. Application to Amide and Ester Synthesis under Neutral Conditions
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On being heated in benzene in the presence of tris(methoxyphenyl)bismuthanes 1b-1e, primary carboxylic acids are selectively activated to couple with amines and alcohols to produce the corresponding amides and esters in satisfactory yields, while secondary, tertiary and aromatic carboxylic acids remain unaffected. 2-Benzylmalonic acid is similarly converted into its corresponding diamides and diesters, but 2,2-dibenzylmalonic acid suffers extensive decarboxylation and, in the presence of aromatic olefins, it undergoes a novel -type cycloaddition reaction to form 4-substituted 2,2-dibenzyl-4-butanolides in low to fair yields.
- Ogawa, Takuji,Hikasa, Tetsuya,Ikegami, Tohru,Ono, Noboru,Suzuki, Hitomi
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p. 3473 - 3478
(2007/10/02)
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- Electron-rich Triarylbismuthines as Selective Condensation Reagent under Neutral Conditions. Condensation of Aliphatic Carboxylic Acids with Amines and Alcohols
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On heating with amines or alcohols in the presence of tris(2-methoxyphenyl)- or tris(2,6-dimethoxyphenyl)bismuthine, carboxylic acids bearing α-hydrogen are readily converted into the corresponding amides or esters in good yields while those without α-hydrogen remain intact.
- Ogawa, Takuji,Hikasa, Tetsuya,Ikegami, Tohru,Ono, Noboru,Suzuki, Hitomi
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p. 815 - 818
(2007/10/02)
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