- Ethanol-drop grinding approach: Cadmium oxide nanoparticles catalyzed the synthesis of [1,3]dioxolo[g][1]benzopyran-6-carboxylic acids and pyrido[d]pyrimidine-7-carboxylic acids
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Aim and Objective: In the last decades, it has extensively been verified that nanostructured transition metal oxides emerge as inexpensive, available and extremely efficient heterogeneous catalysts in chemical transformations. The high electrical conductivity, high carrier concentration, and improved reactivity in cadmium oxide nanoparticles (CdO NPs) make it as a potential candidate for applications in the fields of nanocatalysis. [1]Benzopyran and pyridopyrimidine derivatives compose major classes of heterocyclic compounds, which have a wide spectrum of biological activities. Materials and Methods: In the present work, we report a facile and highly effective synthesis of 8-aryl-8H-[1,3]dioxolo[4,5-g][1]benzopyran-6-carboxylic acids and 1,3-dimethyl-2,4-dioxo-5-phenyl-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-7-carboxylic acids via CdO NPs catalyzed cyclo condensation reaction of 4-substituted phenylmethylidenepyruvic acids with 3,4-methylenedioxyphenol or 6-amino-1,3-dimethyluracil, which was accomplished under ethanol-drop grinding at room temperature. The described catalyst was prepared successfully by a simple precipitation method and characterized by the Fourier transformed infrared absorption (FT-IR) spectroscopy, X-Ray diffraction (XRD) analytical technique, and scanning electron microscopy (SEM). Results: A number of [1,3]dioxolo[g][1]benzopyran-6-carboxylic acids and pyrido[d]pyrimidine-7-carboxylic acids were effectively synthesized in high yields (96-98%) within short reaction times (10-15 min). All synthesized compounds were well-characterized by IR,1H and13C NMR spectroscopy, and also by elemental analyses. Conclusion: In summary, we have developed a very simple and impressive procedure for the synthesis of 8-aryl-8H-[1,3]dioxolo[4,5-g][1]benzopyran-6-carboxylic acids and 1,3-dimethyl-2,4-dioxo-5-phenyl-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-7-carboxylic acids as biologically interesting structures in the presence of CdO NPs as an efficient recyclable heterogeneous catalyst. The remarkable advantages for the offered protocol compared with traditional methods are short reaction time, good yields of the products, and the ease of operation with simple work-up procedure.
- Dahi-Azar, Saman,Abdolmohammadi, Shahrzad,Mokhtari, Javad
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p. 139 - 147
(2021/03/15)
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- Cyanine-Like Boronic Acid-Derived Salicylidenehydrazone Complexes (Cy-BASHY) for Bioimaging Applications
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Boronic acid-derived salicylidenehydrazone complex (BASHY) dyes with a polymethine backbone were designed to yield efficient red-emitting and two-photon absorbing fluorophores that can be used as markers for astrocytes. The dyes are chemically stable in aqueous solution and do not undergo photodecomposition. Their photophysical properties can be electronically fine-tuned and thereby adapted to potentially different imaging situations and requirements.
- Santos, Fábio M. F.,Domínguez, Zoe,Fernandes, Jo?o P. L.,Parente Carvalho, Cátia,Collado, Daniel,Pérez-Inestrosa, Ezequiel,Pinto, Maria V.,Fernandes, Adelaide,Arteaga, Jesús F.,Pischel, Uwe,Gois, Pedro M. P.
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supporting information
p. 14064 - 14069
(2020/10/06)
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- Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes
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Unprecedented α-imino N-acyl pyrazoles were efficiently and selectively prepared through the 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed reaction of nitrosoarenes with N-acyl pyrazoles via an N-nitroso aldol reaction/dehydration sequence. The α-imino acyl pyrazoles were demonstrated to be new versatile intermediates for practical one-pot syntheses of α-imino amides, dipeptide precursors, esters, and β-amino alcohols. The synthetic method competes with known protocols in terms of ready availability of the reagents and catalyst, mild and catalytic reaction conditions, gram-scale applicability, and scope of the α-imino acid derivatives achievable.
- Volpe, Chiara,Meninno, Sara,Mirra, Giulia,Overgaard, Jacob,Capobianco, Amedeo,Lattanzi, Alessandra
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p. 5305 - 5309
(2019/07/03)
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- Ag/CdS nanocomposite: An efficient recyclable catalyst for the synthesis of novel 8-aryl-8h-[1,3]dioxolo[4,5-g]chromene-6-carboxylic acids under mild reaction conditions
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Aim and Objective: Chromene derivatives are privileged heterocyclic systems that exhibit various types of biological properties such as antioxidant, anticancer, antimicrobial, hypotensive, and local anesthetic. Cadmium sulfide nanoparticles (CdS NPs) as an efficient heterogeneous catalyst is used in various organic transformations because of its certain unique and unusual physico-chemical properties. The effectiveness of catalytic activity of CdS NPs can be improved due to the combined effect of Ag particles. Results: Ag/CdS nanocomposite is a readily available, recyclable, and non-toxic catalyst used for the highly efficient synthesis of novel 8-aryl-8H-[1,3]dioxolo[4,5-g]chromrne-6-carboxylic acids. This reaction is conveniently performed under mild reaction conditions. All synthesized compounds were well characterized by their satisfactory elemental analyses, IR, 1H and 13C NMR spectroscopy. The synthesized catalyst was fully characterized by XRD, SEM, and EDX techniques. Materials and Methods: The present methodology focuses on the condensation reaction of arylmethylidenepyruvic acids with 3,4-methylenedioxyphenol, using a catalytic amount of Ag/CdS nanocomposite (15 mol%) in aqueous media at room temperature to afford 8-aryl-8H-[1,3]dioxolo [4,5-g]chromrne-6-carboxylic acids in high yields (90-97%) within short reaction times (2-4 h). The Ag/CdS nanocomposite was also prepared by an ultrasonic-assisted sol-gel method. Conclusion: In conclusion, we have successfully synthesized novel 8-aryl-8H-[1,3]dioxolo[4,5- g]chromrne-6-carboxylic acid derivatives by the Ag/CdS nanocomposite catalyzed cyclocondensation reaction of arylmethylidenepyruvic acids with 3,4-methylenedioxyphenol under mild reaction conditions. Environmentally benign procedure, high to excellent yields of products, simplicity of operation, and use of readily available and recyclable catalyst are the advantages of this new practical reaction.
- Abdolmohammadi, Shahrzad,Nasrabadi, Seyed Reza Rasouli,Seif, Ahmad,Fard, Narges Elmi
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p. 323 - 328
(2018/08/10)
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- Asymmetric hydrogenation method of alpha-ketone amide compound
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The invention belongs to the field of asymmetric catalysis, and discloses an asymmetric hydrogenation method of an alpha-ketone amide compound. The asymmetric hydrogenation method comprises the following steps that under the existence of a catalyst, alkali and a solvent, an alpha-ketone-beta-alkene amide compound is subjected to reduction in the hydrogen atmosphere, and an alpha-hydroxyl-beta alkene amide compound is obtained; and the catalyst is obtained through complexing of metal iridium salt and a chiral ligand, and the chiral ligand is selected from the following compounds: (the formulasare shown in the description). The asymmetric hydrogenation method is easy to operate, high in conversion rate and selectivity and low in cost, has the advantages of being high in atom economy and environmentally friendly, and has a very good industrialized application prospect.
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Paragraph 0197; 0198; 0199; 0200; 0201
(2018/10/04)
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- Photoactivity hexahydroquinolinone and preparation method thereof
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The invention discloses photoactivity hexahydroquinolinone and a preparation method thereof. The photoactivity hexahydroquinolinone is a diastereoisomer consisting of a compound shown as a formula I and a compound shown as a formula II, wherein a diastere
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Paragraph 0043; 0081; 0084
(2017/07/21)
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- A process for preparing (R) - 2-hydroxy-4-phenyl-butyric acid ethyl ester method (by machine translation)
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The invention provides a process for preparing (R)? 2? Hydroxy? 4? Phenyl ethyl butyrate method of, in a cheap and easily obtained benzald and pyruvic acid as a raw material, by condensation, esterification, biological enzyme-catalyzed asymmetric reduction and double bond hydrogenated four-step efficient reaction, in order to eventually 82% overall yield of optically pure target product obtained (R)? HPBE. (by machine translation)
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Paragraph 0040; 0044; 0045; 0047
(2016/10/10)
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- Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds
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Novel rel-(5R,6S,7S)-2-oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52-70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.
- Lozynskyi, Andrii,Zimenkovsky, Borys,Nektegayev, Ihor,Lesyk, Roman
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- Arylidene Pyruvic Acids Motif in the Synthesis of New 2H,5H-Chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles via Tandem Hetero-Diels-Alder-Hemiacetal Reaction
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We have developed a tandem hetero-Diels-Alder-hemiacetal reaction using arylidene pyruvic acids with 5-(ortho-hydroxybenzylidene)-substituted 4-thioxo-2-thiazolidinones, leading to 6-hydroxy-2-oxo-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-6-carboxylic acids. The stereochemistry of cycloaddition was confirmed by NMR spectra and a single-crystal x-ray diffraction analysis.
- Lozynskyi, Andrii,Zimenkovsky, Borys,Gzella, Andrzej K.,Lesyk, Roman
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p. 2266 - 2270
(2015/09/22)
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- Unusual direction of cyclocondensation of 1-(4-chlorophenyl)-3,5-diamino-1, 2,4-triazole, pyruvic acid, and aldehydes
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The reactivity of 1-(4-chlorophenyl)-3,5-diamino-1,2,4-triazole in multicomponent reactions with pyruvic acid and aldehydes and in two-component reactions with arylidenepyruvic acid was studied. The unusual direction of these treatments leading to the formation of unprecedented 3-[5-amino-1-(4- chlorophenyl)-1,2,4-triazol-3-ylamino]-5-arylfuran-2-ones instead of triazolopyrimidine or triazolylpyrrolone derivatives was found and discussed. Georg Thieme Verlag Stuttgart.
- Sakhno, Yana I.,Desenko, Sergey M.,Shishkina, Svetlana V.,Shishkin, Oleg V.,Musatov, Vladimir I.,Chebanov, Valentyn A.
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scheme or table
p. 1120 - 1124
(2011/05/14)
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- Novel 4-N-substituted aryl but-3-ene-1,2-dione derivatives of piperazinyloxazolidinones as antibacterial agents
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Novel (5S)-N-[3-(3-fluoro-4-{4-[2-oxo-4-(substituted aryl)-but-3-enoyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 3a-j analogues were synthesized and their in vitro antibacterial activity was evaluated. Most of the compounds of series showed superior in vitro activity against Gram-positive resistant strains than linezolid. Compound 3f is the most potent compound in the series with 0.04-0.39 μg/mL MIC.
- Varshney, Vandana,Mishra, Nripendra N.,Shukla, Praveen K.,Sahu, Devi P.
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scheme or table
p. 6810 - 6812
(2010/06/12)
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