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Chromium photocatalysis: accessing structural complements to Diels-Alder adducts with electron-deficient dienophiles
A chromium-catalyzed, visible light-activated net [4 + 2] cycloaddition between dienes and electron-deficient alkenes is described. Gathered evidence, via control experiments, isolated intermediates, and measured redox potentials, points to several converging reaction pathways that afford the cyclohexene adducts, including a photochemical [2 + 2] cycloaddition/vinylcyclobutane rearrangement cascade and a substrate excitation/oxidation sequence to a radical cation intermediate. Notably, the accompanying mechanistic stipulations result in a process that yields regioisomeric compounds from those generated by traditional Diels-Alder cycloadditions.
Stevenson, Susan M.,Higgins, Robert F.,Shores, Matthew P.,Ferreira, Eric M.
p. 654 - 660
(2016)
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Blue-light-emitting poly(phenylenevinylene)s with alkoxyphenyl substituents: Synthesis and optical properties
Two new poly(phenylenevinylene)s with alkoxyphenyl subsituents were synthesized and characterized. The polymers were obtained in moderate molecular weights and were amorphous. They showed enhanced solubility in common organic solvents, Tg in th
Spiliopoulos, Ioakim K.,Mikroyannidis, John A.
p. 2149 - 2156
(2002)
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Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system
An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.
Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay
(2021/03/15)

Method for preparing phenyl propenone compound by catalyzing phenylacetylene through molecular sieve
The invention belongs to the field of molecular sieve catalysis and organic synthesis, and discloses a method for preparing a phenyl propenone compound by catalyzing phenylacetylene through a molecular sieve, which comprises the following steps: adding a phenylacetylene compound I, aldehyde II and a molecular sieve catalyst into a small reaction kettle without adding an organic solvent and any other assistants; performing stirring to react for 0.25-6 hours under the condition of heating at 30-90 DEG C, cooling the reaction kettle to room temperature, performing diluting with ethyl acetate, andcentrifugally separating the catalyst to obtain the phenyl allyl ketone compound III. The molecular sieve catalyst provided by the invention is H-beta of which the silica-alumina ratios are respectively 14 and 29. The method is simple in reaction process, high in catalytic activity and selectivity, recyclable, environmentally friendly and capable of achieving large-scale industrial production.
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Paragraph 0076-0080

(2021/03/13)

Synthesis of chalcone derivatives by phthalhydrazide-functionalized tio2-coated nano-fe3o4 as a new heterogeneous catalyst
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
p. 407 - 414
(2021/09/07)

Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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
supporting information

(2021/02/27)

Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.
Upadhyay, Neha,Tilekar, Kalpana,Loiodice, Fulvio,Anisimova, Natalia Yu.,Spirina, Tatiana S.,Sokolova, Darina V.,Smirnova, Galina B.,Choe, Jun-yong,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,Lavecchia, Antonio,Ramaa
(2020/12/21)

Unsaturated ketone compound as well as preparation method and application thereof
The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.
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Paragraph 0219-0222; 0238-0240

(2020/10/30)

Iron(ii)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water
Metalloenzyme is a source of inspiration for chemists who attempt to create versatile synthetic catalysts for aqueous catalysis. Herein, we impart metalloenzyme-like characteristics to a chiral FeII-oxazoline complex by incorporating an Fe(ii) ion into a chiral oxazoline-containing discrete self-folded polymer, to realize highly enantioselective sulfa-Michael addition (SMA) in water. Intrachain FeII-oxazoline complexation together with hydrophobic interactions triggers the self-folding of the oxazoline-containing single polymeric chain in water. The formed FeII-folded single-chain polymeric nanoparticles (SCPNs) significantly accelerate the aqueous asymmetric SMA reaction via a self-folded hydrophobic compartment around the catalytic sites, reminiscent of metalloenzymatic catalysis. In addition, they can be facilely recovered for reuse by simple thermo-controlled separation due to their thermo-responsive properties. Such metallo-folded SCPNs combine the benefits of transition metal- and bio-catalyst, and avoid the tedious procedures of separation, which is a benefit for energy-saving and industrial applications.
Li, Chaoping,Li, Shiye,Tan, Rong,Wang, Jiajun,Wang, Weiying,Yin, Donghong
supporting information
p. 4645 - 4655
(2020/08/10)

Effect of substituents in the A and B rings of chalcones on antiparasite activity
Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.
González, Luis A.,Upegui, Yulieth A.,Rivas, Luis,Echeverri, Fernando,Escobar, Gustavo,Robledo, Sara M.,Qui?ones, Wiston
(2020/08/19)

Micellar Catalysis Strategy of Cross-Condensation Reaction: The Effect of Polar Heads on the Catalytic Properties of Aminoalcohol-Based Surfactants
Abstract: The effect of the polar head and the concentration of quaternary ammonium surfactants (C14EtOH, C14iPrOH, C14PrOH, where, 14 = carbon number iPrOH = iso-propanol, EtOH = ethanol, PrOH = propanol) in micellar cata
Hafidi, Zakaria,Ait Taleb, Mohamed,Amedlous, Abdallah,El Achouri, Mohammed
p. 1309 - 1324
(2019/12/24)

In vitro photodynamic treatment of cancer cells induced by aza-BODIPYs
Two aza-BODIPY photosensitizers (PSs, compounds 7 and 8), featuring an iodine atom on each pyrrolic unit of their structure, were synthesized in fairly good yields starting from commercial products and tested in vitro on two human cancer cell lines (HCT11
Banfi, Stefano,Caruso, Enrico,Malacarne, Miryam Chiara
p. 790 - 799
(2020/07/04)

Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.
Stephan, Marvin,Panther, Jesco,Wilbert, Fabio,Ozog, Pauline,Müller, Thomas J. J.
p. 2086 - 2092
(2020/03/23)

Discovery of Novel Approach for Regioselective Synthesis of Thioxotriaza-Spiro Derivatives via Oxalic Acid
A vital approach for the synthesis of a range of novel thioxotriaza-spiro derivatives is described. These new heterocyclic systems are obtained via oxalic acid catalyzed reaction of α,β-unsaturated ketones in the presence of 5,6-diamino-2-mercaptopyrimidi
Gopinatha, Vindya K.,Mantelingu, Kempegowda,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.,Swarup, Hassan A.
supporting information
p. 2004 - 2009
(2019/10/28)

Synthesis and characterization of new 4,5-dihydropyrazol-1-yl derivatives
In this study, first, a series of chalcone compounds S1–S6 were synthesized from various acetophenone derivatives (acetophenone, p-methyl acetophenone, and p-methoxy acetophenone) and aromatic aldehyde derivatives (benzaldehyde, p-methyl benzaldehyde, and p-methoxy benzaldehyde) by the Claisen–Schmidt condensation reaction. These S1–S6 compounds were then used in the preparation of 4,5-dihydropyrazol-1-yl derivatives S7–S15. Finally, four new compounds S16–S19 were synthesized from compound (S7, S8, S9, and S12) and 2,4-dinitrophenylhydrazine. Therefore, three known and ten new heterocyclic compounds were synthesized and completely characterized using 1H NMR, 13C NMR, IR, and elemental analysis.
?zdemir Güney, Funda,?lhan, ?lhan ?zer,Akko?, Senem
p. 2417 - 2424
(2019/06/27)

Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
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
supporting information
p. 2348 - 2351
(2019/02/27)

1-Arylvinyl formats: A New CO Source and Ketone Source in Carbonylative Synthesis of Chalcone Derivatives
1-Arylvinyl formates as a kind of new CO surrogate have been explored for the first time. Most of the known CO precursors usually produce undesired residuals, which have to be removed. In this strategy, after CO release, the in situ generated acetophenones from 1-arylvinyl formates can be successfully applied as a good ketone source in the synthesis of chalcones with benzaldehydes via a palladium-catalyzed reductive carbonylation reaction. A variety of chalcones were isolated in satisfactory to good yields with good substrates compatibilities under mild conditions.
Qi, Xinxin,Lai, Ming,Zhu, Min-Jie,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
p. 5252 - 5255
(2019/02/25)

Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group
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
supporting information
p. 5801 - 5806
(2019/08/02)

Design, synthesis, and biological evaluation of novel thienopyrimidine derivatives as PI3Kα inhibitors
Three series of novel thienopyrimidine derivatives 9a-l, 15a-l, and 18a-h were designed and synthesized, and their IC50 values against four cancer cell lines HepG-2, A549, PC-3, and MCF-7 were evaluated. Most compounds show moderate cytotoxicity against the tested cancer cell lines. The most promising compound 9a showed moderate activity with IC50 values of 12.32 ± 0.96, 11.30 ± 1.19, 14.69 ± 1.32, and 9.80 ± 0.93 μM, respectively. The inhibitory activities of compounds 9a and 15a against PI3Kα and mTOR kinase were further evaluated. Compound 9a exhibited PI3Kα kinase inhibitory activity with IC50 of 9.47 ± 0.63 μM. In addition, docking studies of compounds 9a and 15a were also investigated.
Yu, Lide,Wang, Qinqin,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Fang, Yuanying,Zhu, Wufu,Zheng, Pengwu
(2019/10/02)

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
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
supporting information
p. 3567 - 3574
(2019/04/14)

Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
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
supporting information
p. 2003 - 2006
(2018/04/16)

Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
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
p. 3368 - 3376
(2017/05/22)

Graphene-supported ZnO nanoparticles: An efficient heterogeneous catalyst for the Claisen-Schmidt condensation reaction without additional base
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
supporting information
p. 3984 - 3988
(2017/09/26)

Catalytic Synthesis of Chalcones and Pyrazolines Using Nanorod Vanadatesulfuric Acid: An Efficient and Reusable Catalyst
Nanorod vanadatesulfuric acid (VSA NRs), as a recyclable and ecologically benign catalyst, was used for the one-pot synthesis of chalcones and 1,3,5-triaryl-2-pyrazolines (TAPs). Chalcones were prepared via the condensation of substituted acetophenones with aryl-aldehydes under solvent-free conditions. Subsequently, the synthesized chalcones were used for the catalytic synthesis of TAPs via two-component condensation with phenyl hydrazine in refluxing ethanol. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate of high purity. Compared to conventional procedures, the present protocol offers several advantages such as simplicity of the procedure, appropriate reaction times, high to excellent yields, easily work-up, recoverability, and reusability of the catalyst, and simple purification of the products.
Nasr-Esfahani, Masoud,Daghaghale, Mona,Taei, Mahbube
p. 17 - 24
(2017/01/17)

An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O
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
p. 1441 - 1448
(2017/09/25)

Synthesis of α,β-unsaturated ketones from alkynes and aldehydes over Hβ zeolite under solvent-free conditions
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
p. 58137 - 58141
(2016/07/07)

A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition
For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.
Muthuvel,Dineshkumar,Thirumurthy,Rajasri,Thirunarayanan
p. 252 - 260
(2017/01/18)

The cascade synthesis of α,β-unsaturated ketones via oxidative C-C coupling of ketones and primary alcohols over a ceria catalyst
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
p. 1693 - 1700
(2016/04/05)

Method for preparing chalcone compound
The invention relates to a method for preparing a chalcone compound. The method utilizes organic solutions of acetophenone or its derivative and benzyl alcohol or its derivative as reaction substrates and a metallic oxide as a catalyst to prepare the chalcone compound through oxidative condensation. The method comprises mixing acetophenone or its derivative, benzyl alcohol or its derivative and the metallic oxide in an organic solvent, putting the mixture into a pressure container, sealing the pressure container, stirring the mixture at a temperature of 40-150 DEG C for 0.5-24h and separating the reaction product to obtain the chalcone compound. The method has the advantages of easy separation of the product from the catalyst, catalyst recycle, simple reaction process and operation easiness and has a chalcone yield of 66%.
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Paragraph 0072-0073

(2017/02/28)

ALLOSTERIC INHIBITORS OF ATYPICAL PROTEIN KINASES C
The invention provides specific small molecule compounds that allosterically regulate the activity of atypical protein kinase C, their use as a medicament, and their use in the treatment and prevention of allergic, inflammatory and autoimmune disorders, cancer, hyperproliferation, sepsis, viral and protozoan infections, dementing diseases, metabolic, sclerotic and osteoporotic disorders.
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Paragraph 0086; 0108; 0133

(2015/06/08)

Bio-derived ZnO nanoflower: A highly efficient catalyst for the synthesis of chalcone derivatives
The green, eco-friendly synthesis of ZnO nanoparticles using the peel of Musa balbisiana and their use as nanocatalysts in the synthesis of chalcones derivatives is reported here. Bio-derived ZnO nanoparticles were characterized by XRD, XPS, FTIR, SEM, BET and TEM techniques. The single step condensation of substituted aryl carbonyls is an attractive feature to obtain substituted chalcones in 88-98% yields in less than 2 min under microwave irradiation in solvent free conditions. A short reaction time with excellent yields of chalcones is the main advantage of our study.
Tamuly, Chandan,Saikia, Indranirekha,Hazarika, Moushumi,Bordoloi, Manobjyoti,Hussain, Najrul,Das, Manash R.,Deka, Kaustavmoni
p. 8604 - 8608
(2015/03/05)

Synthesis and antifungal activity of chalcone derivatives
In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifunga
Zheng, Yuanyuan,Wang, Xuesong,Gao, Sumei,Ma, Min,Ren, Guiming,Liu, Huabing,Chen, Xiaohong
p. 1804 - 1810
(2015/03/04)

Co-N-C Catalyst for C-C Coupling Reactions: On the Catalytic Performance and Active Sites
C-C bond-forming reactions are important in chemistry for construction of complex large molecules from readily available simple substrates. However, they usually involve the employment of organic halides and suffer from toxic or environmental issues. We report an efficient and environmentally benign methodology-aerobic oxidative cross-coupling of primary and secondary alcohols-to directly produce α,β-unsaturated ketones that are key intermediates for synthesis of agrochemical, pharmaceutical, and other fine chemicals. A noble-metal-free Co-N-C catalyst, derived from pyrolysis of cobalt-phenanthroline complexes on a mesoporous carbon support, is developed toward the target reactions and shows high catalytic activity (turnover frequency of 3.8 s-1 based on Co single atoms, surpassing the state of art in the literature), good recyclability, and wide applicability to diverse substrates (28 examples). The active sites in the Co-N-C catalyst are proposed to be Co single atoms bonded with N within graphitic sheets.
Zhang, Leilei,Wang, Aiqin,Wang, Wentao,Huang, Yanqiang,Liu, Xiaoyan,Miao, Shu,Liu, Jingyue,Zhang, Tao
p. 6563 - 6572
(2015/11/18)

Photocatalytic dehalogenation of vicinal dibromo compounds utilizing sexithiophene and visible-light irradiation
The reductive dehalogenation of a variety of vicinal-dibromide compounds has been accomplished through the use of α-sexithiophene as an organophotocatalyst. This photocatalytic system brings about the desired transformations in good yields, using low catalyst loadings and short reaction times. To help shed light on the efficiency of this process, we have studied the kinetics of the key mechanistic steps utilizing a combination of steady-state/time-resolved fluorescence and laser flash photolysis techniques.
McTiernan, Christopher D.,Pitre, Spencer P.,Scaiano, Juan C.
p. 4034 - 4039
(2015/02/19)

Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
Nano titania-supported sulfonic acid (n-TSA) has been easily prepared from the reaction of nano titania (titanium oxide) with chlorosulfonic acid as sulfonating agent and characterized by the FT-IR spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD) and thermal gravimetric analysis (TGA). The catalytic activity of n-TSA was investigated in the synthesis of important organic derivatives such as pyrimidones, benzothiazoles and chalcones. All of the reactions are very fast and the yields are good to excellent. The catalyst was easily separated and reused for several runs without appreciable loss of its catalytic activity.
Rahmani, Salman,Amoozadeh, Ali,Kolvari, Eskandar
p. 184 - 188
(2014/11/08)

Graphene based material as a base catalyst for solvent free Aldol condensation and Knoevenagel reaction at room temperature
Graphene oxide (GO) acts as a highly active heterogeneous base catalyst for a wide variety of reactions. Here we have described the catalytic activities of GO in the condensation reaction of various substituted benzaldehydes with acetophenone (aldol condensation) and with active methylene compound malononitrile (Knoevenagel reaction) at room temperature under solvent free condition. GO is characterized by powder X-ray diffraction (XRD), UV-visible spectra, Fourier transform infrared spectroscopy (FT-IR) and AFM. The experimental results showed that the GO had higher catalytic activity and it can be recycled without significant loss of its activity.
Islam, Sk Manirul,Roy, Anupam Singha,Dey, Ram Chandra,Paul, Sumantra
p. 66 - 73
(2014/08/05)

Discovery and optimization of 1,3,5-trisubstituted pyrazolines as potent and highly selective allosteric inhibitors of protein kinase C-χ
There is increasing evidence that the atypical protein kinase C, PKCχ, might be a therapeutic target in pulmonary and hepatic inflammatory diseases. However, targeting the highly conserved ATP-binding pocket in the catalytic domain held little promise to
Abdel-Halim, Mohammad,Diesel, Britta,Kiemer, Alexandra K.,Abadi, Ashraf H.,Hartmann, Rolf W.,Engel, Matthias
supporting information
p. 6513 - 6530
(2014/10/15)

Synthesis, antimicrobial and DFT studies of novel fused thiazolopyrimidine derivatives
The reaction of dihydropyrimidine-2(1H)-thione 4, obtained by the condensation of chalcone 3 with thiourea, with chloroacetic acid and 1,2-dibromoethane furnished compounds 5 and 6 and not their respective isomers 8 and 9. The regiochemistry of the cycliz
Gupta, Richa,Chaudhary, Ram Pal
p. 207 - 214
(2013/09/02)

Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system
An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.
Khaligh, Nader Ghaffari,Mihankhah, Taraneh
p. 2167 - 2173
(2014/01/06)

Novel and green approach for the nanocrystalline magnesium oxide synthesis and its catalytic performance in Claisen-Schmidt condensation
Magnesium oxide is one of the most promising solid base material having catalytic applications. A novel, simple, efficient, inexpensive, additives free and green synthesis protocol for magnesium oxide nano-particles using concentrated solar energy has been reported. Using magnesium acetate and 1, 4-butanediol magnesium oxide nanoparticles in the range of 5-20 nm was prepared. The driving force for the nanoparticles synthesis was obtained by using concentrated solar energy as a dual energy source in the form of radiational and thermal effect. The resulting magnesium oxide nanoparticles are found to be excellent and reusable catalyst for the Claisen-Schmidt condensation under solvent free condition.
Patil, Aniruddha B.,Bhanage, Bhalchandra M.
p. 79 - 83
(2013/06/27)

Preheated fly-ash catalyzed aldol condensation: Efficient synthesis of chalcones and antimicrobial activities of some 3-thienyl chalcones
In the present study we have prepared a series of some chalcones using solvent - free Aldol - condensation by microwave irradiation. The yields of the ketones are more than 60%. The synthesised chalcones were characterized by their analytical, physical and spectral data. The antimicrobial activities of substituted styryl 3-thienyl ketones have been studied using Bauer-Kirby method.
Arulkumaran, Ranganathan,Vijayakumar, Sambandhamoorthy,Sakthinathan, S. Pazhanivel,Kamalakkannan, Dakshnamoorthy,Ranganathan, Kaliyaperumal,Suresh, Ramamoorthy,Sundararajan, Rajasekaran,Vanangamudi, Ganesan,Thirunarayanan, Ganesamoorthy
p. 1684 - 1690
(2013/09/24)

Synthesis and biological evaluation of some new 4-aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone by conventional and microwave methods and their biological activities
4-Aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone/4-aryl-3-chloro-1-(4,6- diaryl pyrimidine)-2-azetidinone were prepared by reaction of appropriate 2-(methoxy phenylideneamino)-4-diaryl pyrimidine (Schiff base) and acetyl chloride/chloroacetylchloride in dim
Sharma, Sharda,Jain, Renuka,Sharma, Vikas,Chawla, Chetali
p. 221 - 229
(2013/06/04)

Palladium-catalyzed oxidative carbonylative coupling reactions of arylboronic acids with styrenes to chalcones under mild aerobic conditions
Do the coupling: A palladium-catalyzed oxidative carbonylative coupling process of arylboronic acid with styrenes to chalcone has been developed. The reactions proceed under mild conditions using air as the terminal oxidant reagent.
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
experimental part
p. 282 - 285
(2012/04/18)

Silicotungstic acid catalysed Claisen Schmidt condensation reaction: An efficient protocol for synthesis of 1,3-diaryl-2-propenones
An efficient and clean synthesis of 1,3-diaryl-2-propenones has been carried out by Claisen Schmidt condensation reaction of aryl methyl ketones with a series of aromatic aldehydes at room temperature in the presence of the catalyst silicotungstic acid (STA). This method provides an ecofriendly, chemoselective, efficient and green synthesis of 1,3-diaryl-2-propenones in excellent yields.
Rajput, Jaspreet Kaur,Kaur, Gagandeep
experimental part
p. 646 - 649
(2012/02/15)

Synthesis of chalcones with anticancer activities
Several chalcones were synthesized and their in vitro cytotoxicity against various human cell lines, including human breast adenocarcinoma cell line MCF-7, human lung adenocarcinoma cell line A549, human prostate cancer cell line PC3, human adenocarcinoma cell line HT-29 (colorectal cancer) and human normal liver cell line WRL-68 was evaluated. Most of the compounds being active cytotoxic agents, four of them with minimal IC50 values were chosen and studied in detail with MCF-7 cells. The compounds 1, 5, 23, and 25 were capable in eliciting apoptosis in MCF-7 cells as shown by multiparameter cytotoxicity assay and caspase-3/7, -8, and -9 activities (p 0.05). The ROS level showed 1.3-fold increase (p 0.05) at the low concentrations used and thus it was concluded that the compounds increased the ROS level eventually leading to apoptosis in MCF-7 cells through intrinsic as well as extrinsic pathways.
Syam, Suvitha,Abdelwahab, Siddig Ibrahim,Al-Mamary, Mohammed Ali,Mohan, Syam
experimental part
p. 6179 - 6195
(2012/09/07)

Synthesis and in vitro antimicrobial activity of novel 2-(3-oxo-1,3- diarylpropylthio)acetic acid derivatives
A series of novel 2-(3-oxo-1,3-diarylpropylthio)acetic acid derivatives (3a-l) were prepared by base catalyzed addition of thioglycolic acid to chalcones (1a-l). The antibacterial activities of synthesized compounds were screened against human pathogenic microorganisms by employing the disk-diffusion technique. For the active compounds, also minimum inhibitory concentrations (MICs) were determined.
Gezegen, Hayreddin,Karaman, Isa,Ceylan, Mustafa,Dilmac, Merve
p. 893 - 900
(2012/10/30)

Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols
Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.
Xu, Weiliang,Zhou, Yonggui,Wang, Ruimin,Wu, Guotao,Chen, Ping
supporting information; experimental part
p. 367 - 371
(2012/01/13)

Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5- dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 μM for EGFR and IC50 = 1.07 μM for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 μM, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
Qiu, Ke-Ming,Wang, Hai-Hong,Wang, Li-Ming,Luo, Yin,Yang, Xian-Hui,Wang, Xiao-Ming,Zhu, Hai-Liang
experimental part
p. 2010 - 2018
(2012/05/04)

Study on comparison of reducing ability of three organic hydride compounds
Selective reduction of three kinds of substrates were studied to evaluate the reducing abilities of N,N-dimethyl-benzimidazolidine (DMBI), 2-phenylbenzimidazoline (PBI) and 2-phenylbenzothiazoline (PBT). As hydride donors, these three five-membered heterocyclic compounds performed different reducing abilities depending on the substrates.
Feng, Yi-Si,Yang, Chun-Yan,Huang, Qiang,Xu, Hua-Jian
body text
p. 5053 - 5059
(2012/07/28)

Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
experimental part
p. 368 - 377
(2012/07/31)

The effects of solvent on switchable stereoselectivity: Copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands
A highly enantioselective copper-catalyzed conjugate addition of diethylzinc to acyclic aromatic enones was developed with phosphoramidite ligands bearing a D2-symmetric biphenyl backbone. This type of reaction demonstrated that toluene and THF solvents can completely reverse the absolute configuration of the products, thus simplifying the process of accessing either enantiomer (S: 92% ee, 94% yield; R: 99% ee, 96% yield).
Yu, Han,Xie, Fang,Ma, Zhenni,Liu, Yangang,Zhang, Wanbin
supporting information; experimental part
p. 5137 - 5142
(2012/08/07)