- A catalytic regioselective procedure for the synthesis of aryl oximes in the presence of palladium nanoparticles
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The synthesis of aryl oximes from aryl aldehyde derivatives was carried out using hydroxylamine hydrochloride and aluminum oxy hydroxide-supported palladium (Pd/AlO(OH) nanoparticles. The procedure is revealed via the regioselective synthesis of oxime der
- Demir, Emine,Goksu, Haydar,Orhan, Ersin
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- On the mixed oxides-supported niobium catalyst towards benzylamine oxidation
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A series of mixed oxides-supported niobium-based catalysts has been synthesized and applied towards oxidation reactions of benzylamine derivatives. Under the optimized reaction conditions, the selectivity to oxime enhanced, leading to the main product with up to 72 %. Moreover, even α-substituted benzylamines were well tolerated and led to oximes in good isolated yields. It is important to mention; four equivalents of the harmless and inexpensive hydrogen peroxide were employed as oxidizing agent. Mechanism hypothesis suggested that the reaction proceed to selective benzylamine oxidation into nitroso intermediate, following by formation of the corresponding oxime tautomer mediated by an unstable water produced by NbOx supported catalyst. This consists the first mixed oxides-supported niobium-based catalyst for selective oxidation of benzylamines to oximes.
- Granato, álisson Silva,de Carvalho, Gustavo S. Gon?alves,Fonseca, Carla G.,Adrio, Javier,Leit?o, Alexandre A.,Amarante, Giovanni Wilson
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p. 118 - 125
(2020/09/11)
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- The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water
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The synthesis of oximes from aryl aldehydes was prepared using hydroxylamine hydrochloride. The obtained oxime compounds were synthesized at maximum efficiency in mineral water at room temperature. The developed method is economical, practical and environmentally friendly. All of the aldehydes were converted the oxime a method using local sources and useful for industrial applications is introduced in the literature. Graphic abstract: In this study, addition elimination reaction, one of the important reactions of organic chemistry, was carried out using local sources. With this reaction, aryl oximes were obtained from aryl aldehydes in mineral water under catalyst-free conditions.[Figure not available: see fulltext.]
- Goksu, H.,Orhan, E.
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- Poly(N-vinylimidazole): A biocompatible and biodegradable functional polymer, metal-free, and highly recyclable heterogeneous catalyst for the mechanochemical synthesis of oximes
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The catalytic activity of poly(N-vinylimidazole), a biocompatible and biodegradable synthetic functional polymer, was investigated for the synthesis of oximes as an efficient, halogen-free, and reusable heterogeneous catalyst. The corresponding oximes were afforded in high to excellent yields at room temperature and in short times using the planetary ball mill technique. Some merits, such as the short reaction times and good yields for poorly active carbonyl compounds, and avoiding toxic, expensive, metal-containing catalysts, and hazardous and flammable solvents, can be mentioned for the current catalytic synthesis of the oximes. Furthermore, the heterogeneous organocatalyst could be easily separated after the reaction, and the regenerated catalyst was reused several times with no significant loss of its catalytic activity.
- Fahim, Hoda,Ghaffari Khaligh, Nader,Gorjian, Hayedeh
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p. 2007 - 2012
(2022/01/08)
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- Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents
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Objective: A new family of 3′-(Mono, di or tri-substituted phenyl)-4′-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. Methods: A synthetic reaction based on 1,3-dipolar cycloaddition mechanism was applied for the regiospecific formation of various spiroisoxazolines. The activity of the newly synthesized compounds was determined using in vitro cyclooxygenase inhibition assay. The toxicity of the compounds was evaluated by MTT assay. In addition, induction of apoptosis, and expression levels of Bax, Bcl-2 and caspase-3 mRNA in MCF-7 cells were evaluated following exposure to compound 9f. The docking calculations and molecular dynamics simulation were performed to study the most probable modes of interactions of compound 9f upon binding to COX-2 enzyme. Results: The docking results showed that the synthesized compounds were able to form hydrogen bonds with COX-2 involving methyl sulfonyl, spiroisoxazoline, meta-methoxy and fluoro functional groups. Spiroisoxazoline derivatives containing methoxy group at the C-3′ phenyl ring meta position (9f and 9g) showed superior selectivity with higher potency of inhibiting COX-2 enzyme. Furthermore, compound 9f, which possesses 3,4-dimethoxyphenyl on C-3′ carbon atom of isoxazoline ring, exhibited the highest COX-2 inhibitory activity, and also displayed the most potent cytotoxicity on MCF-7 cells with an IC50 value of 0.03 ± 0.01 μM, comparable with that of doxorubicin (IC50 of 0.062 ± 0.012 μM). The results indicated that compound 9f could promote apoptosis. Also, compared to the control group, the mRNA expression of Bax and caspase-3 significantly increased, while that of Bcl-2 significantly decreased upon exposure to compound 9f which may propose the activation of mitochondrial-associated pathway as the mechanism of observed apoptosis. Conclusion: In vitro biological evaluations accompanied with in silico studies revealed that indanone tricyclic spiroisoxazoline derivatives are good candidates for the development of new anti-inflammatory and anticancer (colorectal and breast) agents.
- Abolhasani, Hoda,Zarghi, Afshin,Komeili Movahhed, Tahereh,Abolhasani, Ahmad,Daraei, Bahram,Dastmalchi, Siavoush
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- Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B
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A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.
- Ur Rasool, Javeed,Sawhney, Gifty,Shaikh, Majeed,Nalli, Yedukondalu,Madishetti, Sreedhar,Ahmed, Zabeer,Ali, Asif
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- A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
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A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.
- Jaganmohan, Chikkanti,Vinay Kumar,Venkateshwarlu,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara Rao,Raghunadh, Akula,Tadiparthi, Krishnaji
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supporting information
p. 2163 - 2170
(2020/06/10)
-
- Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis
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Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.
- Calixto, Stephane Lima,Carvalho, Guilherme da Silva Louren?o,Coimbra, Elaine Soares,Granato, Juliana da Trindade,Louren?o, Maria Cristina da Silva,Wardell, James,da Costa, Cristiane Fran?a,de Souza, Marcus Vinicius Nora
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- Microwave synthesis method of benzaldoxime compounds
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The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.
- -
-
Paragraph 0072-0075
(2020/12/08)
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- Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime
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An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.
- Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
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p. 230 - 249
(2019/03/28)
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- A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2
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A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.
- Jiang, Ying,Sun, Bing,Fang, Wan-Yin,Qin, Hua-Li
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p. 3190 - 3194
(2019/05/21)
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- Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
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Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 3723 - 3735
(2019/09/30)
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- Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate
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Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.
- Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.
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- Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
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The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 4226 - 4235
(2018/07/06)
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- Preparation method for p-chlorophenylnitromethane
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The invention relates to a preparation method for p-chlorophenylnitromethane, and belongs to the field of pharmaceutical pesticide intermediates. The method provided by the invention does not need a plurality of recrystallization, has a simple process, an
- -
-
Paragraph 0040-0057
(2018/09/21)
-
- Continuous Platform to Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor
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The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction is reported. A uniquely designed pipes-in-series plug-flow tube reactor addresses a range of process challenges, including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.
- Tsukanov, Sergey V.,Johnson, Martin D.,May, Scott A.,Kolis, Stanley P.,Yates, Matthew H.,Johnston, Jeffrey N.
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supporting information
p. 971 - 977
(2018/08/28)
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- Synthesis and cytotoxic evaluation of undecenoic acid-based oxime esters
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A series of undecenoic acid-based aldoxime esters have been synthesized using various substituted benzaldehydes and undecenoic acid. These oxime esters have been evaluated for their cytotoxic activities against HeLa, B16-F10, SKOV3, MCF7 and CHO-K1 normal cell line using MTT assay. Most of the synthesized compounds exhibit cytotoxicity. Particularly, 2,3-dimethoxy (IC50 value 12.48μM) and 3-methoxy (IC50 value 13.58μM) derivatives exhibit promising activities against SKOV3 cell lines. All the synthesized compounds are non-toxic towards the Chinese hamster ovary (CHO-K1) normal cell line.
- Vijayendar, Venepally,Kaki, Shiva Shanker,Vamshi Krishna,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
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p. 1015 - 1022
(2019/05/22)
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- An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
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A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
- Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
-
supporting information
p. 1990 - 1995
(2017/06/09)
-
- Synthesis, characterization, antimicrobial activity, and QSAR studies of some new 6-substituted phenyl 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino [5,6-d]isoxazoles
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3-(4-Chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d] isoxazoles were synthesized from the reaction of (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol with substituted phenylboronic acids. Crystal structure of 1-(4-(3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d]isoxazol-6-yl)phenyl) ethanone was studied and the values of selected bond distances (?), bond angles (°), and dihedral angles (°) were found in agreement with the calculated (DFT, B3LYP/6-311++G(d,p)) values. Antimicrobial activity of these new compounds was also studied against a panel of microorganisms including Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, Streptococcus mutans, and Candida albicans. Most of the dioxaborepines exhibited fair activities against these microorganisms. The pMIC values of the compounds were first correlated with Hammett polar substituent constant (σ) together with lipophilic constant (π) and statistically significant 2D correlations were obtained. In addition, the pMIC values of the compounds were correlated with some theoretical descriptors and fair 2D-QSAR models with clogP, SAA, and μ as independent variables were obtained.
- Pir, Meryem,Agirbas, Hikmet,Budak, Fatma,Sahin, Onur
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- Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof
-
The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.
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-
Paragraph 0235; 0236; 0250; 0251
(2017/02/28)
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- Synthesis of new dithiolethione and methanethiosulfonate systems endowed with pharmaceutical interest
-
Here we report synthetic methodology affording in the most efficient way the rapid preparation of new dithiolethiones (DTTs) and methanethiosulfonates (MTSs). These were evaluated as STAT3 inhibitors since these electrophilic systems could react with thio
- Gabriele, Elena,Porta, Federica,Facchetti, Giorgio,Galli, Corinna,Gelain, Arianna,Meneghetti, Fiorella,Rimoldi, Isabella,Romeo, Sergio,Villa, Stefania,Ricci, Chiara,Ferri, Nicola,Asai, Akira,Barlocco, Daniela,Sparatore, Anna
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p. 235 - 250
(2017/03/09)
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- Effect of novel triazole-amino acid hybrids on growth and virulence of Candida species: in vitro and in vivo studies
-
The increasing incidence of human candidiasis and the tendency of Candida species to become resistant to existing chemotherapies are well-recognized health problems. The present study demonstrates the successful synthesis of novel triazole-amino acid hybrids with potent in vitro and in vivo inhibitory activity against Candida species. Particularly, compounds 68 and 70 showed potent in vitro activity against fluconazole (FLC) resistant as well as sensitive clinical isolates of Candida albicans. Time kill curve analysis of lead inhibitors 68 and 70 showed their fungistatic nature. Secretion of hydrolytic enzymes, mainly proteinases and phospholipases, decreased considerably in the presence of 68 and 70 indicating their interference in fungal virulence. TEM analysis of Candida cells exposed to compounds 68 and 70 clearly showed morphological changes and intracellular damage as their possible mode of action. A preliminary mechanistic study carried out on the two most effective inhibitors (68 and 70) revealed the inhibition of ergosterol biosynthesis thereby causing the cells to lose their integrity and viability. The selected compounds did not show significant cytotoxicity up to a concentration of 200 μg mL?1 in the HEK293 cell line. An in silico analysis of 68 and 70 binding to a modeled C. albicans CYP51 showed critical H-bonding as well as hydrophobic interactions with the important active site residues indicating the basis of their anti-Candida role. Studies on the larvae of Galleria mellonella showed that the selected inhibitors (68 and 70) were non-toxic, did not provoke an immune response and significantly reduced Candida proliferation in vivo.
- Aneja, Babita,Irfan, Mohammad,Kapil, Charu,Jairajpuri, Mohamad Aman,Maguire, Ronan,Kavanagh, Kevin,Rizvi, M. Moshahid A.,Manzoor, Nikhat,Azam, Amir,Abid, Mohammad
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p. 10599 - 10619
(2016/11/30)
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- POLYCYCLIC PYRAZOLINONE DERIVATIVE AND HERBICIDE COMPRISING SAME AS EFFECTIVE COMPONENT THEREOF
-
Provided are a polycyclic pyrazolinone derivative indicated by general formula (1) (in the formula, R1, X1, X2, X3, and Y indicate the definitions provided in the Specification) and a herbicide comprising same as effective component thereof.
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-
Paragraph 0941; 0942
(2016/02/19)
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- Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis
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Mitogenicity is the ability of the natural or synthetic compounds to induce cell division or proliferation. A series of salicylic acid derivatives containing isoxazoline moiety (8a-j) were synthesized and their immunopharmacological activities targeting lymphocyte proliferation and angiogenesis were evaluated. The compounds 8a-j mitogenicity were investigated on immunological cells that include human peripheral blood lymphocytes and murine splenocytes in-vitro. The results implicate that among the series of 8a-j, compound 8e showed a potent proliferative response on both human and murine lymphocytes. The proliferative index of the compound 8e was comparable to the reference mitogen Con A and mitogenecity is due to increased secretion IL-2. In-vivo CAM and rat corneal angiogenesis assays were performed to assess the compound's effect on endothelial cell migration and proliferation which inferred that 8e also induces the proliferation of endothelial cells. The study reports the synthetic immunostimulatory and pro-angiogenic activity of novel mitogen 8e which could be translated into new drug in future.
- Puttaswamy, Naveen,Pavan Kumar,Al-Ghorbani, Mohammed,Vigneshwaran,Prabhakar,Khanum, Shaukath Ara
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p. 153 - 161
(2016/05/02)
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- Synthesis, characterization, antimicrobial activity, and QSAR studies on substituted oxadiazaboroles
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This paper presents the synthesis and in vitro antimicrobial activity studies of 3,4,5-trisubstituted 4,5-dihydro-1,2,4,5-oxadiazaboroles (4) and 3,5-disubstituted 4,5-dihydro-1,2,4,5-oxadiazaboroles (7). The antimicrobial activities of the compounds were
- Pir, Meryem,Agirbas, Hikmet,Budak, Fatma,Ilter, Merve
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p. 1794 - 1812
(2016/10/03)
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- Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
-
supporting information
p. 7397 - 7401
(2015/07/15)
-
- Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
-
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
-
supporting information
p. 7397 - 7401
(2015/11/27)
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- Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes
-
A novel, transition-metal free, rapid approach for selective oxidation of aliphatic and benzylic amines to oximes is described. The dodecanebis(peroxoic acid)-DMF combination efficiently oxidizes various aliphatic amines at 50 °C temperature to give 100% conversion in 20 min with high oxime selectivity. The peroxy acid used here shows exceptional stability at room temperature and is non-shock sensitive in nature, which was confirmed by differential scanning colorimetric (DSC) analysis.
- Patil, Vilas V.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
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p. 6677 - 6682
(2015/08/06)
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- Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid
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Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.
- Aghapour, Ghasem,Abbaszadeh, Zeinab
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p. 1464 - 1470
(2015/09/01)
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- ZnO Nanotube as reusable catalyst in the efficient and selective oximation reaction of carbonyl groups under solvent free conditions
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A convenient and efficient procedure for the selective protection of carbonyl groups in the presence of ZnO nanotube, as reusable eco-friendly catalyst under solvent free conditions is described. The salient features of this methodology are cheaper process, easy availability of the catalyst, versatility, and the catalyst can be recovered after completion of the reaction and can be recycled without affecting the catalytic property.
- Kiasat, Ali Reza,Javaherian, Mohammad,Daei, Mina,Farbod, Mansoor
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p. 875 - 880
(2015/11/24)
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- 3,5-diarylisoxazoles: A New Entry to Soft Crystal Phase
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This work describes the synthesis and characterization of a new liquid-crystalline compounds based on isoxazoles. Classical synthetic methodologies were employed in the preparation of this compounds, and the [3+2] 1,3-dipolar cycloaddition was the key ste
- Da Rosa, Rafaela R.,Brose, Irwing S.,Vilela, Guilherme D.,Merlo, Aloir A.
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p. 158 - 168
(2015/07/15)
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- Oxime carbamates as potential insecticidal agents: Design, synthesis and biological evaluation
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A series of oxime carbamates derivatives were designed and synthesized as a part of our ongoing search for novel high potential agrochemicals. Their structures were confirmed by 1H NMR, 13C NMR and elemental analysis. The bioassays results indicated that some of the obtained compounds exhibited good insecticidal activity against Heliothis armigera and Plutella xylostella.
- Ke, Shaoyong,Yang, Ziwen,Shi, Liqiao,Liu, Manli,Liang, Ying,Wang, Kaimei,Long, Tong,Jiang, Aibing,Zhang, Zhigang
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p. 771 - 777
(2015/10/05)
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- SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS
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The present invention relates to novel spiro-oxadiazoline compounds that are suitable as agonists or partial agonists of a7-nAChR, and pharmaceutical compositions of the same, methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering a spiro-oxadiazoline cx7-nAChR agonist or partial agonist, to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.
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Paragraph 00202-00203
(2015/05/19)
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- Metal-Free: A novel and efficient aerobic oxidation of primary amines to oximes using N, N', N''-trihydroxyisocyanuric acid and acetaldoxime as catalysts in water
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A general, efficient, and metal-free method for aerobic oxidation of aromatic primary amines to the corresponding oximes catalyzed by N,N',N''-trihydroxyisocyanuric acid and acetaldoxime with water as solvent is described. This practical method can use air as economic and green oxidant, water as green solvent, and tolerates a wide range of substrates, which can afford the target oximes in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.
- Yu, Jiatao,Lu, Ming
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p. 1873 - 1878
(2014/08/18)
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- Dual nature of polyethylene glycol under microwave irradiation for the clean synthesis of oximes
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Polyethylene glycol (PEG-400 and PEG-600) is an efficient, inexpensive, and recyclable homogeneous medium and catalyst (dual nature) for the clean synthesis of oximes (and aldoximes) under microwave irradiation in the absence of acid and base catalysts. Both aliphatic and aromatic aldehydes/ketones give satisfactory results under microwave irradiation within a short time. Graphical abstract: [Figure not available: see fulltext.]
- Dutta, Papia,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli
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p. 505 - 508
(2014/03/21)
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- Microwave-assisted synthesis of fulleropyrazolines/fulleroisoxazolines mediated by (diacetoxyiodo)benzene: A rapid and green procedure
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Microwave as a green, rapid and effective procedure has been applied to the synthesis of fulleropyrazolines/fulleroisoxazolines. The reaction mixtures containing substituted phenylhydrazones/oximes, C60 and PhI(OAc) 2 allowed to achieve products at room temperature in a good yield and short time without any side product.
- Safaei-Ghomi, Javad,Masoomi, Reihaneh
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p. 2954 - 2960
(2014/01/06)
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- Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas disease
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Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5-dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g) was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to 1 μM). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.
- Rodrigues, Giseli Capaci,Feijó, Daniel Ferreira,Bozza, Marcelo Torres,Pan, Peiwen,Vullo, Daniela,Parkkila, Seppo,Supuran, Claudiu T.,Capasso, Clemente,Aguiar, Alcino Palermo,Vermelho, Alane Beatriz
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p. 298 - 308
(2014/02/14)
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- Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene- based chiral sulfides as organocatalysts
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This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps.
- Huang, Meng-Ting,Wu, Hsin-Yi,Chein, Rong-Jie
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supporting information
p. 1101 - 1103
(2014/01/17)
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- Base and solvent mediated decomposition of tosylhydrazones: Highly selective synthesis of N-alkyl substituted hydrazones, dialkylidenehydrazines, and oximes
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Base and solvent mediated decomposition of tosylhydrazones was studied. It was found that reaction of tosylhydrazones in CH3NO2 in the presence of 1 equiv of K2CO3 in 90 °C gave N-alkylated products in 52-96% yield. However, when the same reaction was carried out in mixed solvent of CH3NO2 and dioxane in the presence of 3 equiv of NaOH at 110 °C, dialkylidenehydrazines were obtained in moderate to high yield. If the reaction was carried out in mixed solvent of CH3NO2 and DMSO in the presence of 10 equiv of NaOH at 110 °C, CH3NO2 can act as the precursor of hydroxylamine and corresponding oximes were formed in up to 92% yield.
- Sha, Qiang,Wei, Yunyang
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supporting information
p. 3829 - 3835
(2013/07/05)
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- Selective ammoximation of ketones and aldehydes catalyzed by a trivanadium-substituted polyoxometalate with H2O2 and ammonia
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The ammoximation of different ketones and aldehydes to their corresponding oximes catalyzed by K6[PW9 V3O 40]·4H2O was carried out with hydrogen peroxide and ammonia in isopropanol at room temperature. High yields of oximes were obtained in this catalytic system. This catalytic system was proved to be heterogeneous by the ammoximation activity of removal of catalyst and the elemental analysis of the filtrate after reaction. A possible procedure for the ammoximation catalyzed by K6[PW9V3O40] ·4H2O with H2O2 and NH 3·H2O was proposed. The fresh and used catalysts were characterized by IR and 31P MAS NMR, which revealed the good stability of the catalyst.
- Xue, Xiaoling,Song, Fangyuan,Ma, Baochun,Yu, Yongze,Li, Cheng,Ding, Yong
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- Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
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Nitrones serve as starting materials for the synthesis of many heterocycles. Oxidation of secondary amines using hydrogen peroxide and the catalytic amount of methyltrioxorhenium in ionic liquids is a useful method for the preparation of nitrones. Ultrasonic irradiation and ionic liquids have a positive influence on the reaction. The nitrones required were isolated in good yields. Corresponding hydroxylamines, which can be easily oxidised to nitrones, often accompanied the main products. Methyltrioxorhenium in ionic liquids was re-used in several reaction cycles without any deteriorating effect on the course of the reaction.
- Meciarova, Maria,Mojzesova, Melinda,Sebesta, Radovan
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p. 51 - 58,8
(2020/08/20)
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- An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model
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An unexpected intramolecular cyclization during the reaction of furfurylamine with maleimides is reported as a novel strategy for the efficient green synthesis of the 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton. Under the same reaction conditions, 7-oxabicyclo[2.2.1]hept-5-enes were synthesized when furfurylamine was N-protected by the acetyl group. Both types of bicycloheptenes were screened using the zebrafish model system for genetics and developmental biology. The Royal Society of Chemistry 2013.
- Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.
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supporting information
p. 407 - 411
(2013/02/25)
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- PROCESS FOR THE PREPARATION OF ISOXAZOLYL- METHOXY NICOTINIC ACIDS
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The present invention relates to a process for the preparation of a compound of formula (I) wherein R1 and R2 are as defined herein, which is useful as an intermediate in the preparation of active pharmaceutical compounds.
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Paragraph 0227; 0228
(2013/05/08)
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- PROCESS FOR THE PREPARATION OF ISOXAZOLYL-METHOXY-NICOTINIC ACIDS
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The present invention relates to a process for the preparation of a compound of formula (I) which is useful as an intermediate in the preparation of active pharmaceutical compounds from a compound of formula (IV) wherein R1 and R2 ar
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Page/Page column 35; 36; 37
(2013/05/09)
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- Iodine(III)-Mediated [3 + 2] cyclization for one-pot synthesis of benzo[ d ]isoxazole-4,7-diols in aqueous medium
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A one-pot [3 + 2] cycloadditive synthesis of benzo[d]isoxazole-4,7-diols in aqueous medium was carried out via nitrile oxides and benzoquinone intermediates by taking advantage of iodobenzene diacetate as an oxidant. This method can also be used to synthesize benzodiisoxazole-4,8-diols, isoxazolo[5,4-a]phenazines, and indazole-4,7-diols, which are difficult to obtain by classical methods.
- Hou, Yingwei,Lu, Shichao,Liu, Gang
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p. 8386 - 8395
(2013/09/24)
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- Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant
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Isoxazolines can be efficiently synthesized in good yields via a hypoiodite mediated catalytic oxidative cyclization of aldoximes and alkenes. This reaction involves active iodine species generated in situ from catalytic amounts of KI and Oxone.
- Yoshimura, Akira,Zhu, Chenjie,Middleton, Kyle R.,Todora, Anthony D.,Kastern, Brent J.,Maskaev, Andrey V.,Zhdankin, Viktor V.
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supporting information
p. 4800 - 4802
(2013/06/05)
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- Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes
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Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.
- Yoshimura, Akira,Middleton, Kyle R.,Todora, Anthony D.,Kastern, Brent J.,Koski, Steven R.,Maskaev, Andrey V.,Zhdankin, Viktor V.
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supporting information
p. 4010 - 4013
(2013/09/02)
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- Formation of C-O bond via cross-dehydrogenative coupling between isochroman and oxime under metal-free oxidation conditions
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DDQ-mediated C-O bond formation through cross-dehydrogenative coupling (CDC) reaction without any metal catalyst under mild conditions was developed. Series of isochromans and oximes could be employed as substrates, and the products were obtained in good yields. Georg Thieme Verlag Stuttgart New York.
- He, Hua-Feng,Wang, Kai,Xing, Bo,Sheng, Guorong,Ma, Tingxuan,Bao, Weiliang
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supporting information
p. 211 - 214
(2013/03/13)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0113
(2013/03/26)
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- Highly selective and efficient lewis acid-base catalysts based on lanthanide-containing polyoxometalates for oximation of aldehydes and ketones
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Two lanthanide-containing polyoxometalates (POMs) have been developed as Lewis acid-base catalysts for highly selective and efficient oximation of various aldehydes and ketones under mild conditions. Copyright
- Zhao, Shen,Huang, Lujiang,Song, Yu-Fei
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p. 1659 - 1663
(2013/05/09)
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