- New pyrimidine derivatives as efficient organic inhibitors on mild steel corrosion in acidic medium: Electrochemical, SEM, EDX, AFM and DFT studies
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New pyrimidine derivatives, namely, 7-methoxypyrido [2,3-d]pyrimidin-4-amine (MPPA) and 4-amino-7-methoxypyrido[2,3-d]pyrimidin-2(1H)-one (AMPO) were synthesized and their inhibitive action against the corrosion of mild steel in 15% HCl solution was studi
- Yadav,Kumar,Sinha,Bahadur,Ebenso
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Read Online
- Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations
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A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.
- Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa
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p. 3267 - 3279
(2021/06/17)
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- Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols
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Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.
- Bhattacharyya, Dipanjan,Sarmah, Bikash Kumar,Nandi, Sekhar,Srivastava, Hemant Kumar,Das, Animesh
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supporting information
p. 869 - 875
(2021/02/06)
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- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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supporting information
(2021/02/27)
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- Synthesis of chalcone derivatives by phthalhydrazide-functionalized tio2-coated nano-fe3o4 as a new heterogeneous catalyst
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Phthalhydrazide immobilized on TiO2-coated nano Fe3O4 (Fe3O4-P) was synthesized and characterized by FT-IR, XRD, SEM, EDS and VSM analysis. The resulting magnetic nanocatalyst was used as a catalyst for the synthesis of chalcone derivatives which affords the desired products in good to excellent yields. This catalyst can be isolated readily after completion of the reaction by an external magnetite field and reused several times without significant loss of activity.
- Farahi, Mahnaz,Karami, Bahador,Keshavarz, Raziyeh,Nia, Forough Motamedi
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p. 407 - 414
(2021/09/07)
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- Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions
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High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Qi, Minghui,Wang, Dawei
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- A Remote ‘Imidazole’-Based Ruthenium(II) Para-Cymene Pre-catalyst for the Selective Oxidation Reaction of Alkyl Arenes and Alcohols
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Herein we disclosed the use of a remote ‘imidazole’-based precatalyst [(para-cymene)RuII(L)Cl]+, C-1 where L=2-(4-substituted-phenyl)-1H-imidazo[4,5-f][1,10] phenanthroline) for the selective oxidation of a variety of alkyl arenes/heteroarenes and alcohols to their corresponding aldehydes or ketones in presence of tert-butyl hydroperoxide (TBHP). The remote ‘imidazole’ moiety present in the complex facilitates the activation of oxidant and subsequent generation of active species via the release of para-cymene from C-1, which in-turn was less effective without the ‘imidazole’ moiety. The mechanistic features of C-1 promoted oxidation of alkyl arenes were also assessed from spectroscopic, kinetic, and few control experiments. The substrate scope for C-1 promoted oxidation reaction was assessed based on the selective oxidation of 27-different alkyl arenes/heteroarenes and 25 different alcohols to their corresponding aldehydes/ketones in moderate to good yields.
- Dutta, Manali,Bania, Kusum K.,Pratihar, Sanjay
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p. 926 - 932
(2020/03/05)
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- Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds
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In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.
- Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa
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- Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions
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A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CH3CN. CLN1provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CH3CN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1caused by the ionization or OH-F?interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.
- Bu, Ren,Du, Yanqing,Eerdun, Chaolu,Hu, Mixia,Liang, Fengying,Tsuda, Akihiko,Wang, Meiling
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p. 37463 - 37472
(2020/10/28)
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- β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties
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[Figure not available: see fulltext.] Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.
- Shuvalov, Vladislav Yu.,Elisheva, Valeriya А.,Belousova, Anastasiya S.,Arshinov, Evgenii V.,Glyzdinskaya, Larisa V.,Vorontsova, Marina А.,Chernenko, Sergei А.,Fisyuk, Aleksander S.,Sagitullina, Galina P.
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- On the development of a nucleophilic methylthiolation methodology
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Methylthiolation reactions are usually explored to access organosulfur compounds using methanethiol, an extremely flammable and toxic compound. Herein, methylthiomethyl esters were successfully applied as novel methylthiolation reagents in a low cost, transition-metal-free methodology. These reagents allowed the methylthiolation of a wide scope of chalcones, acyl ester derivatives and Morita-Baylis-Hillman acetates with good group tolerance, affording the methylthiolated products in moderate to excellent yields. The reaction mechanism was investigated through several control experiments, as well as by theoretical calculations employing Density Functional Theory. The results strongly support that a sulfurane and a sulfonium ylide appear as key intermediates and that a Pummerer type rearrangement is also crucial for the formation of this novel reagent. Furthermore, the methylthiolation mechanism is likely to proceed through the nucleophilic attack of the reagent, followed by an entropically favoured step involving the acetate attack to the positively charged species, then releasing the product. This journal is
- Carvalho, Bernardo Basbaum Portinho De Puga,Amaral, Adriane Antonia Pereira,De Castro, Pedro P?ssa,Ferreira, Fernanda Cerqueira Moreira,Horta, Bruno Araújo Cautiero,Amarante, Giovanni Wilson
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p. 5420 - 5426
(2020/08/03)
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- NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS
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The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.
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Paragraph 0361-0362
(2019/11/04)
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- Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
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A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.
- Li, Jimei,Zhang, Jie,Li, Mingfei,Zhang, Chenyang,Yuan, Yongkun,Liu, Renhua
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supporting information
p. 2348 - 2351
(2019/02/27)
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- Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles
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New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.
- Guglielmi, Paolo,Carradori, Simone,Poli, Giulio,Secci, Daniela,Cirilli, Roberto,Rotondi, Giulia,Chimenti, Paola,Petzer, Anél,Petzer, Jacobus P.
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- The role of phosphine ligands in the catalytic systems of the Heck reaction with aromatic carboxylic anhydrides
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The results of a comparative study of phosphine-containing and phosphine-free catalytic systems of the Heck reaction using aromatic carboxylic anhydrides as arylating agents are presented. It was demonstrated that the patterns of diff erential selectivity of the reaction under competition of two aromatic anhydrides or two alkenes are independent of the presence of a tertiary phosphine additive in the system. It was established that palladium complexes with no phosphine ligands in their coordination sphere are catalytically active at the step of activation of aromatic carboxylic anhydride and alkene. The patterns of diff erential selectivity for regioisomers of arylated products provide the evidence of the participation of phosphine-containing anionic palladium complexes in the regioselectivity-determining step of the catalytic cycle. The data obtained are in agreement with the phosphine involvement in the catalyst transformations proceeding outside the main catalytic cycle.
- Lagoda,Larina,Yarosh,Kurokhtina,Schmidt
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p. 817 - 824
(2019/06/03)
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- Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group
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A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Ding, Chengrong
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supporting information
p. 5801 - 5806
(2019/08/02)
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- Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
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The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
- Zhang, Meng-Juan,Li, Hong-Xi,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 3567 - 3574
(2019/04/14)
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- Regiospecific Aza-Michael Addition of 4-Aryl-1 H -1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium
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A novel metal-free and base-mediated method to display the donor ability of 1,2,3-triazoles for the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed. A DABCO-promoted aza-Michael addition of 4-aryl NH-1,2,3-triazoles to α,β-unsaturated ketones (chalcones) is presented. The reactions proceeded with complete regiospecificity in a 3:1 mixture of acetonitrile and methanol at 85 °C to provide 2,4-disubstituted 1,2,3-triazoles as Michael adducts, and the addition products 1,3-diaryl-(4-aryl-2 H -1,2,3-triazol-2-yl)propan-1-ones were isolated in high yields.
- Bhagat, Ujjawal Kumar,Peddinti, Rama Krishna
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- Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
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A number of pyrimidine bridged combretastatin derivatives were designed, synthesized and evaluated for anticancer activities against breast cancer (MCF-7) and lung cancer (A549) cell lines using MTT assays. Most of the synthesized compounds displayed good
- Kumar, Bhupinder,Sharma, Praveen,Gupta, Vivek Prakash,Khullar, Madhu,Singh, Sandeep,Dogra, Nilambra,Kumar, Vinod
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p. 130 - 140
(2018/03/23)
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- Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3-Diols
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A chemo- and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3-diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β-borylation of α,β-unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)-keto–alcohols and (S,S)-diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.
- Gandolfi, Raffaella,Facchetti, Giorgio,Christodoulou, Michael S.,Fusè, Marco,Meneghetti, Fiorella,Rimoldi, Isabella
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p. 393 - 400
(2018/06/04)
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- Synthesis and catalytic reactivity in Friedel–Crafts acylations of monobridged bis(cyclopentadienyl)molybdenum(I) carbonyl complexes
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When the monobridged biscyclopentadienes (C5H5)R(C5H5) [R = C(CH3)2 (1), Si(CH3)2 (2), C(CH2)5 (3)] reacted with Mo(CO)6 in refluxing xylene, the corresponding complexes [(η5-C5H4)2R][Mo(CO)3]2 [R = C(CH3)2 (4), Si(CH3)2 (5), C(CH2)5 (6)] were obtained. These complexes were separated by chromatography and characterized by elemental analysis, IR, and 1H NMR spectroscopy. The molecular structures of 4 and 5 were determined by X-ray diffraction analysis. Friedel–Crafts acylation reactions of anisole derivatives with aromatic or aliphatic acyl chlorides catalyzed by complexes 4–6 showed that all of these monobridged bis(cyclopentadienyl)molybdenum carbonyl complexes have catalytic activity.
- Yan, Xin Long,Zhang, Ning,Hao, Zhi Qiang,Ma, Zhi Hong,Han, Zhan Gang,Zheng, Xue Zhong,Lin, Jin
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
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- Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
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A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
- Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
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supporting information
p. 2003 - 2006
(2018/04/16)
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- Graphene-supported ZnO nanoparticles: An efficient heterogeneous catalyst for the Claisen-Schmidt condensation reaction without additional base
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ZnO nanoparticles supported on reduced graphene oxide (ZnO/RGO) were prepared by the hydrothermal method and characterized by TEM, XPS, XRD, and Raman spectroscopy. As a green catalyst, ZnO/RGO was applied to the Claisen-Schmidt condensation reaction of aryl aldehydes and aryl ketones under microwave irradiation. Therein, chalcone products could be efficiently synthesized and easily separated from the heterogeneous catalysis system. The catalyst could be recycled four times without significant loss of catalytic activity.
- Li, Zhuofei,Zhao, Hongyan,Han, Huatao,Liu, Yang,Song, Jinyi,Guo, Weihao,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 3984 - 3988
(2017/09/26)
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- Design, synthesis and bioactivity of chalcones and its analogues
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The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.
- Niu, Chao,Tuerxuntayi, Adila,Li, Gen,Kabas, Madina,Dong, Chang-Zhi,Aisa, Haji Akber
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supporting information
p. 1533 - 1538
(2017/07/17)
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- 13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles
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A series of chalcones 1-12 were converted to pyrazolines (1Pi-12Pi) by reaction with phenylhydrazine followed by DDQ oxidation to produce the corresponding pyrazoles (1Pz-12Pz). Three 1-phenyl-3-t-butyl-5-arylpyrazoles (13Pz-15Pz) were synthesized using an analogous approach. Molecular modeling studies predicted the 5-aryl group of the pyrazoles for both series to have a torsion angle of 52°-54° whereas the 1-phenyl group was predicted to have 35°-37° torsion angles. The 3-aryl group was predicted to be essentially coplanar (-3°) with the pyrazole system in the first series. 13C NMR data for both series, 1Pz-12Pz and 13Pz-15Pz, were collected in DMSO-d6 at 50°C. A plot of the C4 chemical shifts for 1Pz-12Pz versus Hammet constants for 5-aryl substituents yielded a very good linear correlation (R2=0.96) with a slope of 1.5. The chemical shift data for C4 showed little or no dependence on 3-aryl substituents. The result for 13Pz-15Pz, despite only three points, was consistent with the first series results and yielded a ρ value of 2.0. Distal transmission of substituent effects (5-aryl groups) to C4 of the pyrazole system was reduced by roughly 50-60% of that of the analogous planar isoxazole system, but are not consistent with results for the similarly twisted 4-bromoisoxazoles.
- Hockstedler, Amy N.,Edjah, Beatrice A.,Azhar, Saajid Z.,Mendoza, Hadrian,Brown, Nicole A.,Arrowood, Hayley B.,Clay, Andrew C.,Shah, Anand B.,Duffek, Glenda M.,Cui, Jianmei,Baumstark, Alfons L.
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p. 125 - 131
(2017/04/14)
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- A regioselective and convenient one-pot multicomponent synthesis of 9-amino-3,5-diaryl-4,9-dihydro-5H-[1,2,4]triazolo[5,1-c][1,2,4]triazepine-8-thiol
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An efficient and environment-friendly procedure for the synthesis of a new series of nitrogen bridge-head [1,2,4]triazolo[5,1-c][1,2,4]triazepine derivatives through one-pot three-component reaction of polyfunctional triazole with aromatic aldehydes and acetophenone derivatives using alcoholic sodium hydroxide solution. The same new products were prepared in classical route through reaction of triazole with the corresponding chalcones under the same conditions.
- Moustafa, Amr Hassan,Amer, Amer Anwar
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p. 1102 - 1109
(2017/05/25)
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- Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
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Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
- Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
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p. 3368 - 3376
(2017/05/22)
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- Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
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The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
- Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
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p. 921 - 929
(2017/07/11)
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- Copper(II)-promoted oxidative C-H/C-H cross-coupling for rapid access to aza-BODIPY-indole derivatives with broad optical absorption
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The direct C-H activation of electron-deficient aza-BODIPYs has been effectively achieved via a concise and inexpensive Cu(ii)-promoted oxidative C-H/C-H coupling approach. The resulting indole-aza-BODIPY 6b covers a broad spectrum of 429-900 nm with a FW
- Jiang, Ruyong,Yang, Xiuguang,Wu, Di
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supporting information
p. 6888 - 6891
(2017/09/01)
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- Design, synthesis and molecular docking of novel diarylcyclohexenone and diarylindazole derivatives as tubulin polymerization inhibitors
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New target compounds were designed as inhibitors of tubulin polymerization relying on using two types of ring B models (cyclohexenone and indazole) to replace the central ring in colchicine. Different functional groups (R1) were attached to man
- Ahmed, Riham I.,Osman, Essam Eldin A.,Awadallah, Fadi M.,El-Moghazy, Samir M.
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p. 176 - 188
(2017/11/21)
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- Synthesis, carbonic anhydrase I and II inhibition studies of the 1,3,5-trisubstituted-pyrazolines
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4-(3-(4-Substituted-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl) benzenesulfonamides (9–16) were successfully synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, and HRMS spectra. Carbonic anhydrase I and II inhibitory effects of the compounds were investigated. Ki values of the compounds were in the range of 316.7 ± 9.6–533.1 ± 187.8 nM towards hCA I and 412.5 ± 115.4–624.6 ± 168.2 nM towards hCA II isoenzymes. While Ki values of the reference compound Acetazolamide were 278.8 ± 44.3 nM and 293.4 ± 46.4 nM towards hCA I and hCA II izoenzymes, respectively. Compound 14 with bromine and compound 13 with fluorine substituents can be considered as the leader compounds of the series because of the lowest Ki values in series to make further detailed carbonic anhydrase inhibiton studies.
- Gul, Halise Inci,Mete, Ebru,Taslimi, Parham,Gulcin, Ilhami,Supuran, Claudiu T.
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p. 189 - 192
(2017/11/21)
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- Synthesis and structure-activity relationships of 4-morpholino-7,8-dihydro-5h-thiopyrano[4,3-d] pyrimidine derivatives bearing pyrazoline scaffold
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Phosphatidylinositol 3-kinase/Protein kinase B/Mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway is abnormally active in the growth and proliferation of cancer cells. The inhibition of PI3K kinase can effectively block the conduction of sign
- Wang, Qinqin,Li, Xiaojing,Sun, Chengyu,Zhang, Binliang,Zheng, Pengwu,Zhu, Wufu,Xu, Shan
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- Anchoring pyrazolines on a 2,2′:6′,2″-terpyridine backbone
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Introducing pyrazoline derivatives into the classical 2,2′:6′,2″-terpyridine (2,2′:6′,2″-tpy) backbone leads to the synthesis of a new class of compounds, 4′-pyrazolinyl-2,2′:6′,2″-tpys. Six such derivatives bearing differently substituted pyrazolines hav
- Liu,Li, Li,Xiong, Hangxing,Chan, Corinna,Cheng, Jessica,Zhang, Guoqi
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p. 397 - 403
(2017/08/01)
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- Imidazole-triazine type compound and preparation method and application thereof
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The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.
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Paragraph 0031; 0032; 0033; 0034; 0035; 0037
(2017/10/06)
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- Syntheses, structures and catalytic activity for Friedel-Crafts reactions of substituted indenyl rhenium carbonyl complexes
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The complexes [(η5-C9H6R)Re(CO)3] [R?=?nBu (8), tBu (9), CH(CH2)4 (10), Ph (11), Bz (12), 4-methoxyphenyl (13), 4-chlorophenyl (14)] were synthesized by refluxing substituted indenyl ligands [C9H7R] [R?=?nBu (1), tBu (2), CH(CH2)4 (3), Ph (4), Bz (5), 4-methoxyphenyl (6), 4-chlorophenyl (7)], and Re2(CO)10 in decalin. The molecular structures of 9, 10, 12, and 13 were determined by X-ray diffraction analysis. These four crystals have similar molecular structures of the mononuclear carbonyl complex. In each of these molecules, Re is η5-coordinated to the five-membered ring of the indenyl group. Complexes 8–14 have catalytic activity for Friedel-Crafts reactions of aromatic compounds with a variety of alkylation and acylation reagents. Compared with traditional catalysts, these mononuclear metal carbonyl complexes have obvious advantages such as high activities, mild reaction conditions, high selectivity, and environmentally friendly chemistry.
- Ma, Zhihong,Zhang, Xinli,Wang, Hong,Han, Zhangang,Zheng, Xuezhong,Lin, Jin
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p. 709 - 721
(2017/02/05)
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- An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O
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Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].
- Bhat, Prabhat,Shridhar, Gomathi,Ladage, Savita,Ravishankar, Lakshmy
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p. 1441 - 1448
(2017/09/25)
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- Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts
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A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
- Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Lázaro-Milla, Carlos
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p. 2177 - 2186
(2017/02/26)
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- 2-Oxindole Acts as a Synthon of 2-Aminobenzoyl Anion in the K2CO3-Catalyzed Reaction with Enones: Preparation of 1,4-Diketones Bearing an Amino Group and Their Further Transformations
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A convenient approach for the synthesis of 1,4-diketones bearing an amino group has been developed through the K2CO3-catalyzed reaction of 2-oxindoles with enones with the assistance of atmospheric O2 via sequential Michael addition-oxidation-ring-cleavage process. The further intramolecular reaction leads to the formation of benzoazepinone, quinoline, and 3-oxindole derivatives.
- Miao, Chun-Bao,Zeng, Yu-Mei,Shi, Tong,Liu, Rui,Wei, Peng-Fei,Sun, Xiao-Qiang,Yang, Hai-Tao
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- Synthesis, molecular docking study, and cytotoxic activity of 1,3,5-triaryl pyrazole derivatives
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Synthesis, molecular docking study, and cytotoxic activity of a new group of 1,3,5-triaryl pyrazole derivatives were be studied. The antiproliferative activity of the final compounds were examined in MCF-7, AGS, HT-29 and NIH3T3 cell lines by MTT assay, u
- Ghasemi, Maryam,Ghadbeighi, Sajad,Amirhamzeh, Amirali,Tabatabai, Seyed Abbas,Ostad, Seyed Nasser,Shafiee, Abbas,Amini, Mohsen
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p. 121 - 128
(2016/03/12)
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- Synthesis of novel thiazolylpyrazoline derivatives and evaluation of their antimicrobial activities and cytotoxicities
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Several novel thiazolylpyrazoline derivatives were synthesized by reacting substituted 3,5-diaryl-1-thiocarbamoyl-2-pyrazolines with phenacylbromides. The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and MS spectral data. Their antimicrobial activities against Staphylococcus aureus (ATCC-25923), Enterococcus faecalis (ATCC-29212), Enterococcus faecalis (ATCC-51922), Listeria monocytogenes (ATCC-1911), Klebsiella pneumoniae (ATCC-700603), Pseudomonas aeruginosa (ATCC-27853), Escherichia coli (ATCC-35218), Escherichia coli (ATCC-25922), Candida albicans (ATCC-90028), Candida glabrata (ATCC-90030), Candida krusei (ATCC-6258), and Candida parapsilosis (ATCC-22019) were investigated. The compounds were also studied for their cytotoxic effects using a MTT assay. Compound 7c showed the highest antimicrobial activity, possessing the same potential as chloramphenicol against K. pneumonia, P. aeruginosa, and E. coli (ATCC-25923).
- Tabbi, Aouatef,Kaplancikli, Zafer Asim,Tebbani, Dahmane,Yurtta?, Leyla,Cantürk, Zerrin,Atli, ?zlem,Baysal, Merve,Turan-Zitouni, Gülhan
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p. 641 - 654
(2016/07/06)
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- Facile Microwave-assisted Synthesis of 1,3,5-Trisubstituted Pyrazoline Derivatives Incorporating Sulfonyl Moiety
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We developed an environmentally benign, convenient microwave-assisted process for the construction of 1,3,5-trisubstitued pyrazolines (10a～10f, 11a～11f, 12a～12f, 13a～13f). Chalcones, as the key intermedi- ates, were obtained by the condensation of each of appropriately substituted aromatic aldehydes (1～4) with 4-substituted acetophenones (5a～5f) via a Claisen-Schmidt reaction under the action of microwave irradiation. Cyclization of the chalcones (6a～6f, 7a～7f, 8a～8f, 9a～9f) with p-toluene sulfonhydrazide af- forded 1,3,5-trisubstitued pyrazoline derivatives using microwave-assisted process in 25 min and 140 watt power in glycol. The structures of targeted compounds were established by IR, 1H NMR, MS and ele- mental analysis. The results indicate that microwave-assisted synthetic process presents advantages in terms of enhancement in rate, decrease in reaction time, clean reaction and convenient operation.
- Liu, Fei,Yang, Jin-Feng,Liu, Hong,Wei, Wen-Zhen,Ma, Yan-Mei
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p. 254 - 260
(2016/04/19)
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- Effects of substituents on NMR chemical shifts and mass fragmentation patterns of 1-aryl-3-phenylpropanes
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The 1H and 13C chemical shifts and the mass spectral fragmentation patterns of 1-aryl-3-phenylpropanes with m- or p-substituents (H, NO2, Br, Cl, OCH3, CH3) were studied. The electronic effects of the substi-tuents seemed to be transmitted by the through-space as well as by a through-bond mechanism, resulting in an inverse correlation in the plot of the chemical shift values of i-C vs. the Hammett σ values. The mass spectra showed the substituted benzyl fragments as the base peaks when the substituents were electron donating, whereas the benzyl fragment was observed as the base peaks with the electron-withdrawing substituents.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 538 - 543
(2016/04/26)
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- Substituent-Controlled Chemoselective Cleavage of C = C or Csp2 - C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates
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An unprecedented substituent-controlled chemoselective cleavage of C = C double bond or C(sp2)-C(CO) bond along with aerobic phosphorylation of α,β-unsaturated carbonyl compounds with H-phosphonates through a radical process has been disclosed. The current strategy provides an access to β-ketophosphonates under mild conditions with a wide substrate scope.
- Zhou, Yao,Rao, Changqing,Mai, Shaoyu,Song, Qiuling
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p. 2027 - 2034
(2016/03/15)
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- Iodine-promoted oxidative coupling reaction: a simple and efficient process to access imidazo[1,2-a]pyridines from 2-aminopyridines and chalcones
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A unique and efficient approach has been developed for the synthesis of substituted imidazo[1,2-a]pyridines with aminopyridines and chalcones via a one-pot I2-induced aerobic oxidative coupling. The reported reaction proceeded though a tandem Michael addition followed by an intramolecular oxidative amination with high regioselectivity, yields and good functional group tolerance.
- Xing, Meng-Ming,Xin, Ming,Shen, Chao,Gao, Jian-Rong,Jia, Jian-Hong,Li, Yu-Jin
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supporting information
p. 4201 - 4204
(2016/07/06)
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- Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
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The cyclization of chalcones 3a-3u with 3-hydrazinyl-6-phenylpyridazine 7 under basic condition led to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50values of 8.33, 1.67 and 10?μM against HepG-2, MCF-7 and CaCo-2 cancer cell lines, respectively. Moreover, their antiproliferative activity was due to apoptosis rather than necrosis induction except compound 8h which exhibited equal apoptotic and necrotic properties. Compound 8k showed 5 fold increase in caspase-3 activity indicating that the apoptosis proceeds via caspase-3 activation.
- George, Riham F.,Fouad, Marwa A.,Gomaa, Iman E.O.
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- Synthesis of some novel 5,7-disubstituted-2-phenyl-5H-[1,3,4]thiadiazolo [3,2-a]pyrimidine derivatives and evaluation of their biological activity
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Background: In the present study, a series of 5,7-disubstituted-2-phenyl-5H-[1,3,4] thiadiazolo[3,2-a]pyrimidine derivatives have been reported. The title compounds were synthesized by the reaction of substituted chalcones with 5-phenyl-1,3,4-thiadiazol-2-amine in n-butanol. Methods: All reactions were performed at reflux temperature and the synthesized compounds were characterized by IR, NMR and Mass spectroscopic techniques. Results: The synthesized compounds were screened for their antimicrobial and antioxidant activities. The compounds displayed significant antimicrobial and antioxidant activities. Additionally, the selected compounds were screened for in silico molecular docking studies. Conclusion: In the present work, we have reported an efficient method for the synthesis of some new 5,7-disubstituted-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives. Collectively, all the current computational insights support the in vitro observations seen for antimicrobial and antioxidant agents. Further, the pyrimidine derivatives might act as potential specific inhibitors of G6P synthase thereby facilitating its biological activities. From the activity results, it has been concluded that among the studied compounds, compounds 5b, 5d, 5e, 5g, 5i, 5m and 5n could serve as potential antimicrobial and antioxidant agents.
- Venkatesh, Talavara,Bodke, Yadav D.,Joy, Nibin M.,Vinoda,Shiralgi, Yallappa,Dhananjaya
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p. 661 - 671
(2017/01/13)
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- The cascade synthesis of α,β-unsaturated ketones via oxidative C-C coupling of ketones and primary alcohols over a ceria catalyst
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We herein report the oxidative C-C coupling of ketones and primary alcohols to produce α,β-unsaturated ketones in the absence of base additives. This cascade synthetic reaction was conducted at 150 °C in 12 h using a heterogeneous CeO2 catalyst. The conversion of acetophenone reached 74% with 89% selectivity to chalcone. A correlation between the CeO2 crystal plane and catalytic performance is established as the catalytic activities decrease in the sequence of (110) > (111) > (100). Characterization using Raman spectroscopy, CO2 temperature-programmed desorption (CO2-TPD), and in situ active site-capping tests has shown that the unusual catalysis of the CeO2 catalyst is attributed to the coexistence of basic and redox active sites. These sites synergistically catalyze the oxidation of alcohols to aldehydes and the aldol condensation to ketones. Moreover, the CeO2 catalyst can be reused several times after calcination to remove the surface-adsorbed substances.
- Zhang, Zhixin,Wang, Yehong,Wang, Min,Lu, Jianmin,Zhang, Chaofeng,Li, Lihua,Jiang, Jingyang,Wang, Feng
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p. 1693 - 1700
(2016/04/05)
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- Synthesis of α,β-unsaturated ketones from alkynes and aldehydes over Hβ zeolite under solvent-free conditions
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A facile Hβ zeolite-catalyzed strategy has been successfully developed for the synthesis of α,β-unsaturated ketones from alkynes and aldehydes under solvent-free conditions. The reaction proceeds via tandem hydration/condensation of alkynes with aldehydes to afford a range of α,β-unsaturated carbonyls in good to excellent yields. This journal is.
- Mameda, Naresh,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Nama, Narender
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p. 58137 - 58141
(2016/07/07)
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- Application of bis(oxazoline) in asymmetric β-amination of chalcones
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An effective enantioselective β-amination of chalcones with N-bromosuccinimide into β-imidoketones using a bis(oxazoline) ligand is described. A wide variety of β-imidoketone derivatives containing various functional groups can be obtained with high enantioselectivities. The products are highly valuable molecules regarding their vast applications as building blocks of drugs and biologically active compounds.
- Deng, Tao,Wang, Hongjun,Cai, Chun
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supporting information
p. 102 - 105
(2015/02/19)
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- Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
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Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.
- Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
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p. 8072 - 8093
(2015/05/20)
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