- Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
-
3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
- Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
-
supporting information
p. 4422 - 4429
(2021/08/07)
-
- 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
-
-
- TBHP/Cu(OAc)2 mediated oxidation of pyrazolines: A convenient method for the preparation of pyrazoles
-
An efficient and simple oxidative protocol has been developed for the preparation of pyrazoles from pyrazolines mediated by TBHP/Cu(OAc)2 at room temperature. The present protocol has been successfully applied for the preparation of various pyrazole compounds from heterocyclic pyrazolines.
- Kolla, Sai Teja,Somanaboina, Ramya,Bhimapaka, China Raju
-
supporting information
p. 1425 - 1432
(2021/02/27)
-
- Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones
-
The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.
- Yue, Guizhou,Jiang, Dan,Dou, Zhengjie,Li, Sicheng,Feng, Juhua,Zhang, Li,Chen, Huabao,Yang, Chunping,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Lu, Cuifen
-
supporting information
p. 11712 - 11718
(2021/07/12)
-
- Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
-
We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
- Kurouchi, Hiroaki,Sai, Masahiro
-
supporting information
p. 3585 - 3591
(2021/06/27)
-
- Double-edged Swords: Diaryl pyrazoline thiazolidinediones synchronously targeting cancer epigenetics and angiogenesis
-
In the present study, two novel series of compounds incorporating naphthyl and pyridyl linker were synthesized and biological assays revealed 5-((6-(2-(5-(2-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy) naphthalene-2-yl)methylene)thiazolidine-2,4-dione (14b) as the most potent dual inhibitors of vascular endothelial growth factors receptor-2 (VEGFR-2) and histone deacetylase 4 (HDAC4). Compounds 13b, 14b, 17f, and 21f were found to stabilize HDAC4; where, pyridyl linker swords were endowed with higher stabilization effects than naphthyl linker. Also, 13b and 14b showed best inhibitory activity on VEGFR-2 as compared to others. Compound 14b was most potent as evident by in-vitro and in-vivo biological assessments. It displayed anti-angiogenic potential by inhibiting endothelial cell proliferation, migration, tube formation and also suppressed new capillary formation in the growing chick chorioallantoic membranes (CAMs). It showed selectivity and potency towards HDAC4 as compared to other HDAC isoforms. Compound 14b (25 mg/kg, i.p.) also indicated exceptional antitumor efficacy on in-vivo animal xenograft model of human colorectal adenocarcinoma (HT-29). The mechanism of action of 14b was also confirmed by western blot.
- Kumar, Alan P.,Meyer-Almes, Franz-Josef,Ramaa, C. S.,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
-
-
- Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
-
One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
- Biswal, Priyabrata,Chandrasekhar, Vadapalli,Meher, Sushanta Kumar,Samser, Shaikh,Venkatasubbaiah, Krishnan
-
supporting information
(2021/11/01)
-
- Synthesis and Biological Evaluation of Pyrazoline and Pyrrolidine-2,5-dione Hybrids as Potential Antitumor Agents
-
In search of novel and effective antitumor agents, pyrazoline-substituted pyrrolidine-2,5-dione hybrids were designed, synthesized and evaluated in silico, in vitro and in vivo for anticancer efficacy. All the compounds exhibited remarkable cytotoxic effects in MCF7 and HT29 cells. The excellent antiproliferative activity toward MCF7 (IC50=0.78±0.01 μM), HT29 (IC50=0.92±0.15 μM) and K562 (IC50=47.25±1.24 μM) cell lines, prompted us to further investigate the antitumor effects of the best compound S2 (1-(2-(3-(4-fluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione). In cell-cycle analysis, S2 was found to disrupt the growth phases with increased cell population in G1/G0 phase and decreased cell population in G2/M phase. The excellent in vitro effects were also supported by inhibition of anti-apoptotic protein Bcl-2. In vivo tumor regression studies of S2 in HT29 xenograft nude mice, exhibited equivalent and promising tumor regression with maximum TGI, 66 % (i. p. route) and 60 % (oral route) at 50 mg kg?1 dose by both the routes, indicating oral bioavailability and antitumor efficacy. These findings advocate that hybridization of pyrazoline and pyrrolidine-2,5-dioes holds promise for the development of more potent and less toxic anticancer agents.
- Anisimova, Natalia Y.,Choe, Jun-yong,Lavecchia, Antonio,Loiodice, Fulvio,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,S Ramaa, C.,Smirnova, Galina B.,Sokolova, Darina V.,Spirina, Tatiana S.,Tilekar, Kalpana,Upadhyay, Neha
-
p. 1813 - 1825
(2020/09/07)
-
- Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
-
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
- Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
-
supporting information
p. 5040 - 5045
(2019/07/03)
-
- 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)
-
- Straightforward synthesis of quinolines from enones and 2-aminobenzyl alcohols using an iridium-catalyzed transfer hydrogenative strategy
-
A new protocol for the direct synthesis of quinolines from enones and 2-aminobenzyl alcohols via iridium-catalyzed transfer hydrogenative reactions has been demonstrated. This method employs easily available [IrCp?Cl2]2/t-BuOK as the efficient catalyst system, proceeding with the merits of high step- and atom efficiency, mild reaction conditions and operational simplicity. The experimental studies suggest that the reactions start with transfer hydrogenation, followed by the Friedl?nder reaction to give the final products.
- Xiong, Biao,Wang, Yingying,Liu, Yuan,Bao, Yandan,Liu, Zhaoguo,Zhang, Yanan,Ling, Yong
-
supporting information
p. 5707 - 5711
(2018/08/17)
-
- 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)
-
- Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles
-
Hetaryl-substituted thiochalcones react with acetylenic mono- and diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24 h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three minutes and, in most cases, an improvement in the yield of the [4+2]-cycloadduct was observed. The reactions with methyl propiolate occurred regioselectively and the 3-carboxylates were formed exclusively.
- Mlostoń, Grzegorz,Grzelak, Paulina,Heimgartner, Heinz
-
-
- 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
-
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
-
p. 1102 - 1109
(2017/05/25)
-
- General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis
-
[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.
- Lei, Tao,Zhou, Chao,Huang, Mao-Yong,Zhao, Lei-Min,Yang, Bing,Ye, Chen,Xiao, Hongyan,Meng, Qing-Yuan,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
-
supporting information
p. 15407 - 15410
(2017/11/13)
-
- High efficient Aldol condensation reaction utilizing modified calcium oxide as stable solid base catalyst
-
Aldol condensation of acetophenone and benzaldehyde, as well as various benzaldehydes was carried out efficiently to produce chalcone with a good selectivity and high yields by using modified CaO as a solid base catalyst. Stability and catalytic activity of commercial CaO were significantly improved after modifying calcium oxide with bromobenzene in a simple way. An Aldol yield higher than 98.9% was obtained after the reaction was conducted for 3 h. This time interval is considerably shorter when compared to a period of 12 h needed for the commercial CaO to reach 92.1% yield under optimum activation. The high catalytic activity of modified CaO suggests that heterogeneous aldolisation was greatly improved by changing its hydrophilic properties. The influence of several reaction parameters, such as temperature and catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic sites of modified CaO are resistant to CO2 and moisture. The type of aldehyde has great influence on the yield of Aldol condensation. Based on the results of characterization by Fourier transform-infrared spectrometry (FT-IR) and thermogravimetric measurements (TG), it was concluded that the modifier was chemically bonded to the surface of CaO and nearly no Ca(OH)2 was formed during the modification process.
- Wang, Jin,Yan, Tianlan,Tang, Ying,Miao, Yanqing
-
p. 439 - 445
(2016/08/06)
-
- Study of Regiochemical Trends During the Synthesis of Furan and 5-(p-chlorophenyl)Furan Containing Novel Spiropyrrolidine Library Through 1,3-dipolar Cycloaddition Reactions
-
A new class of functionalized furan and 5-(p-chlorophenyl)furan containing spiropyrrolidines has been synthesized in moderate to excellent yields by the one-pot, three-component 1,3-dipolar cycloaddition reaction of in situ generated azomethine ylides with various furan/aryl furan-substituted chalcones as dipolarophiles. The effect of electron deficient substituents at the fifth position of the furan ring in the chalcone on the regiochemistry of the cycloaddition formed was studied. The structures of the newly synthesized cycloaddicts were proved by analytical and spectral data.
- Mallya, Sahana,Kalluraya, Balakrishna,Jois, H. S. Vidyashree
-
p. 1859 - 1865
(2016/11/23)
-
- Direct Regioselective [3 + 2]-Cyclization Reactions of Ambivalent Electrophilic/Nucleophilic β-Chlorovinyl Dithianes: Access to Cyclopentene Derivatives
-
The highly regioselective and operationally straightforward [3 + 2] cyclizations of β-chlorovinyl dithianes with α,β-unsaturated carbonyl compounds have been developed. This protocol provides direct access to highly functionalized cyclopentenes with perfect chemo- and regioselectivities under extremely mild reaction conditions. In particular, the unprecedented cyclization allows for the selective preparation of hydroxylated cyclopentenes.
- Liang, Yongping,Lai, Junshan,Liu, Teng,Tang, Shouchu
-
supporting information
p. 5086 - 5089
(2016/10/14)
-
- 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)
-
- Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
-
Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
- Li, Liang,Liu, Yidong,Peng, Yang,Yu, Lei,Wu, Xiaoyan,Yan, Hailong
-
supporting information
p. 331 - 335
(2016/01/25)
-
- 4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model
-
Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones.
- Roman, Bart I.,De Ryck, Tine,Patronov, Atanas,Slavov, Svetoslav H.,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
-
p. 627 - 639
(2015/08/03)
-
- Synthesis and screening of antimicrobial activity of novel pyrrolylpyrazole derivatives
-
Novel pyrrolyl-pyrazole derivatives (5a-k) were synthesized by reacting substituted chalcones (3a-k) and 4-pyrrol-1-yl benzoic acid hydrazide (4) in ethanol. Purity of newly synthesized compounds were confirmed by TLC and melting point. The structures of all newly synthesized compounds were confirmed by spectral study such as IR, 1H NMR and Mass spectroscopy. The title compounds were screened for their antibacterial and antitubercular activities.
- Hallikeri,Joshi, Shrinivas D.,Kumar, Devendra,Kulkarni,Selvam, Theivendren Paneer
-
p. 261 - 264
(2019/01/21)
-
- 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)
-
- Ugi three-component coupling reaction for the synthesis of 2-(6-oxo-11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazocin-5(6H)-yl) -2-phenylacetamide derivatives
-
A three-component, four center Ugi reaction of 3-(1-(2-aminophenyl)-5- phenyl-1H-pyrrol-2-yl)propanoic acid with aromatic aldehyde and t-butyl isocyanide has been achieved to produce a novel class of N-tert-butyl-2-(6-oxo- 11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazacine-5(6H)-yl) -2-phenylacetamides in moderate to good yields. 2013 Elsevier Ltd. All rights reserved.
- Reddy, P. Lakshmi,Ashok Kumar,Lakshmi Devi,Reddy, T. Veera,Reddy, B.V. Subba,Narender
-
supporting information
p. 657 - 661
(2014/01/23)
-
- Synthesis, characterization and crystal structure of 4,7-dioxo-7- phenylheptanoic acid
-
4,7-Dioxo-7-phenylheptanoic acid was synthesized from acetophenone and furfural. Firstly, acetophenone reacted with furfural in the presence of sodium hydroxide at room temperature, then the product of the first step was transformed into 4,7-dioxo-7-phenylheptanoic by the process of hydrolyzation by using acetic acid and hydrochloric acid. The product was characterized by 1H NMR and LC-MS. The crystal structure of compound 1 was investigated using X-ray diffraction and SHELXTL-97 software and it was first reported here. The result indicated that compound 1 crystallized in the monoclinic system, space group P2(1)/c with a = 5.3007 (14), b = 28.405 (8), c = 7.679(2) ?, V = 1130.4 (5) ?3; Z 4.
- Zhuang, Wei,Ju, Chao-Fan,Zhang, Xiu-Qin,Xiao, Jian,Wang, Kai
-
p. 3116 - 3118
(2014/06/09)
-
- Efficient aldol condensation by using modified CaO as solid-base catalysts
-
A new type of solid-base catalyst for aldol condensation reaction was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyze the aldol condensation of acetophenone and benzaldehyde to produce chalcone with a high conversion and good selectivity. The catalyst gave a higher yield (90.5%) of chalcone than commercial CaO. The high catalytic activity and stability of this catalyst was related to the organic modifier with a hydrophilic functional group that improved the diffusion of grease to the catalyst surface and prevented its hydration. The influence of several reaction parameters, such as temperature, catalyst loading and the moisture absorption rate of modified CaO, was investigated. From the results, the basic centers of modified CaO are stable and hardly poisoned by CO2 unlike commercial CaO. The catalyst was completely recyclable without significant loss in activity up to five reaction cycles. Moreover, this catalyst showed a promising future in providing an environmentally clean process for the industrial sector. Springer Science+Business Media B.V. 2011.
- Tang, Ying,Chen, Gang,Lu, Yong
-
experimental part
p. 937 - 946
(2012/08/28)
-
- Photodimerization of heteroaryl chalcones: Comparative antimicrobial activities of chalcones and their photoproducts
-
The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop- 2-en-1-one (2) gave b-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl) bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave d-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop- 2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di (1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity. Springer Science+Business Media, LLC 2011.
- Nagwanshi, Rekha,Bakhru, Meena,Jain, Shubha
-
p. 1587 - 1596
(2012/11/07)
-
- Synthesis and selective inhibitory activity against human COX-1 of novel 1-(4-substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline derivatives
-
Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2-pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1-thiocarbamoyl-2- pyrazolines with the ethyl ester of α-bromo-pyruvic acid. The synthesized compounds were confirmed by spectroscopic data and assayed to evaluate their in vitro ability to inhibit both isoforms of human cyclooxygenase (hCOX). Some derivatives (compounds 5, 6, 13, 16, and 17) displayed promising selectivity against hCOX-1 in the micromolar range and were shown to have a selectivity index similar or better than the reference drugs (indometacin, diclofenac). The introduction of a phenyl or a 4-F-phenyl ring on the C5 associated with a 4-substituted phenyl or a heteroaryl group on the C3 of (4-substituted-thiazol- 2-yl)pyrazoline derivatives improved the activity against hCOX-1. Thanks to these preliminary results it could be possible to extend our knowledge of the pharmacophoric requirements for the discovery of new pyrazoline-based hCOX-1 inhibitors. Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2- pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1- thiocarbamoyl-2-pyrazolines with the ethyl ester of α-bromo-pyruvic acid. Some derivatives displayed promising selectivity against human cyclooxygenase 1 (hCOX-1) in the micromolar range, with a selectivity index similar or better than the reference drugs, indometacin and diclofenac. Copyright
- Carradori, Simone,Secci, Daniela,Bolasco, Adriana,De Monte, Celeste,Yá?ez, Matilde
-
p. 973 - 979
(2013/02/23)
-
- Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic carbonates and enones
-
The phosphine-catalyzed annulations between Morita-Baylis-Hillman adduct carbonates and enones are reported. Under the catalysis of PBu3 (20 mol %), cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions chemoselectively occur depending on the substituent variation of both the carbonate and enone. These reactions provide efficient syntheses of highly functionalized cyclopentenes and cyclopentanes.
- Zhou, Rong,Wang, Jianfang,Song, Haibin,He, Zhengjie
-
supporting information; scheme or table
p. 580 - 583
(2011/04/23)
-
- Discovery of S-nitrosoglutathione reductase inhibitors: Potential agents for the treatment of asthma and other inflammatory diseases
-
S-Nitrosoglutathione reductase (GSNOR) regulates S-nitrosothiols (SNOs) and nitric oxide (NO) in vivo through catabolism of S-nitrosoglutathione (GSNO). GSNOR and the anti-inflammatory and smooth muscle relaxant activities of SNOs, GSNO, and NO play significant roles in pulmonary, cardiovascular, and gastrointestinal function. In GSNOR knockout mice, basal airway tone is reduced and the response to challenge with bronchoconstrictors or airway allergens is attenuated. Consequently, GSNOR has emerged as an attractive therapeutic target for several clinically important human diseases. As such, small molecule inhibitors of GSNOR were developed. These GSNOR inhibitors were potent, selective, and efficacious in animal models of inflammatory disease characterized by reduced levels of GSNO and bioavailable NO. N6022, a potent and reversible GSNOR inhibitor, reduced bronchoconstriction and pulmonary inflammation in a mouse model of asthma and demonstrated an acceptable safety profile. N6022 is currently in clinical development as a potential agent for the treatment of acute asthma.
- Sun, Xicheng,Wasley, Jan W. F.,Qiu, Jian,Blonder, Joan P.,Stout, Adam M.,Green, Louis S.,Strong, Sarah A.,Colagiovanni, Dorothy B.,Richards, Jane P.,Mutka, Sarah C.,Chun, Lawrence,Rosenthal, Gary J.
-
scheme or table
p. 402 - 406
(2011/06/26)
-
- Synthesis of 1,3,5-trisubstituted pyrazolines as antimicrobial. and antiinflammatory agents
-
A series of pyrazolines (2a-j) have been synthesized and evaluated for their antimicrobial and antiinflammatory activities. The structures of the synthesized compounds have been confirmed on the basis of physical and spectral data. Compounds 2b, 2c, 2e and 2g have shown moderate antibacterial activity. None of the synthesized compounds showed antifungal activity. Compounds 2b and 2c exhibited significant antiinflammatory activity.
- Nuthana,Harinadha Babu,Madhava Reddy
-
p. 283 - 284
(2013/09/24)
-
- Tandem [4 + 1 + 1] annulation and metal-free aerobic oxidative aromatization: Straightforward synthesis of highly substituted phenols from one aldehyde and two ketones
-
Polysubstituted phenols are efficiently assembled from one aldehyde and two different methyl ketones in a one-pot operation via a newly base-induced regiospecific [4 + 1 + 1] annulation and sequential metal-free oxidative aromatization using molecular oxygen (from air) as the sole oxidant at room temperature.
- Wang, Mang,Fu, Zhenqian,Feng, Hui,Dong, Ying,Liu, Jun,Liu, Qun
-
supporting information; experimental part
p. 9061 - 9063
(2011/02/17)
-
- 3-Aryl-5-furylpyrazolines and their biological activities
-
Aryl-furyl substituted pyrazolines 2a-c and 4a-c were prepared by the reaction of α,βunsaturated carbonyl compounds with hydrazine or phenyl hydrazine. N-chloroacetyl derivatives 3a-c were obtained by the N-acetylation of 2a-c. The antibacterial activities of synthesized pyrazolines were examined by employing the disk-diffusion technique. All synthesized compounds showed antibacterial effects in 1200 μg concentration.
- Cetin, Ahmet,Cansiz,Digrak
-
p. 345 - 347
(2007/10/03)
-
- Some furfural derivatives as nitrification inhibitors
-
Three series of furfural derivatives, namely N-O-furfural oxime ethers, furfural Schiff bases (furfurylidene anilines), and furfural chalcones, have been synthesized and evaluated for nitrification inhibition activity in laboratory incubation studies in typic Ustocrept soil. Furfural oxime ethers and furfural Schiff bases showed potential activity, but furfural chalcones were only mildly active. N-O-ethyl furfural oxime among the oxime ethers, and furfurylidine-4-chloroaniline among the furfural Schiff bases, performed the best. These two compounds showed more than 50% nitrification inhibition on the 45th day at 5% dose as compared to 73% inhibition by nitrapyrin. Activity of furfural oxime ethers decreased with an increase in carbon atoms in the N-O-alkyl side chain. Introduction of a chlorine atom in the phenyl ring of furfurylidene anilines increased the persistence of their activity. N-O-Ethyl furfural oxime and furfurylidine-4-chloroaniline coated urea performed at par with their application in solution form. Ethyl and N-O-isopropyl oxime, as well as chloro- and nitro-substituted Schiff bases, did not reveal any phytotoxicity (adverse effect on germination) on chickpea seeds (Cicer arietinum) even at the highest dose (40 ppm, soil basis).
- Datta,Walia,Parmar
-
p. 4726 - 4731
(2007/10/03)
-
- The treatment of pests using certain ethylenically-unsaturated carbonyl compounds
-
A pesticidal composition comprising an inert carrier and, as active ingredient, an αβ-unsaturated carbonyl compound selected from:(i) compounds of the formula I wherein R1 is a phenyl group optionally substituted with 1 or 2 chlorine atoms, a naphthyl group or a furyl group optionally substituted by 1 or 2 methyl groups, R2 is a group selected from phenyl, furyl, thienyl, furfuryl, thien-2-ylmethyl or a group of the formula(vi) 2-cyclohexenone; and(vii) 5-phenyl-3-formyl-pyran-4-one. The composition has use particularly in the treatment of pests such as insects and acarids. The invention also provides compounds of formula I above whereinR1 is 2-naphthyl and R2 is furfuryl; orR1 is phenyl and R2 is fur-3-yl; orR2 is fur-3-yl and R1 is 2,5-dimethylfur-3-yl; orR1 is phenyl and R2 is 3,4-methylenedioxyphenyl.
- -
-
-
- Synthesis of 3-Cyano-2-methylpyridines Substituted with Heteroaromatics
-
A series of title compounds were easily prepared by the sonication of α,β-unsaturated carbonyl compound in acetonitril in the presence of potassium t-butoxide.
- Shibata, Katsuyoshi,Katsuyama, Isamu,Matsui, Masaki,Muramatsu, Hiroshiga
-
p. 161 - 165
(2007/10/02)
-
- 1,4-benzoquinone: A new selective reagent for oxidation of alcohols
-
The utility of 1,4-benzoquinone as a highly selective reagent for the oxidation of aryl conjugated primary allylic alcohols in the presence of benzylic and aryl conjugated secondary allylic alcohols is demonstrated. The reaction is clean, convenient and results in moderate to high yields.
- Kulkarni,Mathew
-
p. 4497 - 4500
(2007/10/02)
-
- Reaction of α-Halogeno Ketones with Carbonyl Compounds Promoted by CeI3, CeCl3-NaI,or CeCl3-SnCl2
-
Reaction of α-halogeno ketones with aldehydes in the presence of CeI3 in tetrahydrofuran is found to give α,β-unsaturated ketones in excellent yields under mild conditions.In contrast, treatment of α-halogeno ketones and carbonyl compounds with CeCl3-NaI or CeCl3-SnCl2 affords β-hydroxy ketones in good yields.It is assumed that these reactions proceed via cerium enolates.The combined reagents, however, cannot be applied to a Reformatsky-type reaction.Regiospecific and aldehyde chemoselective aldol synthesis are also described.
- Fukuzawa, Shin-ichi,Tsuruta, Takuya,Fujinami, Tatsuo,Sakai, Shizuyoshi
-
p. 1473 - 1478
(2007/10/02)
-
- FLUORIDE ION INDUCED REACTIONS OF ORGANOSILANES: THE PREPARATION OF MONO AND DICARBONYL COMPOUNDS FROM β-KETOSILANES.
-
β-ketosilanes react with a variety of carbon electrophiles in the presence of CsF to give mono- and dicarbonyl derivatives in reasonably good yields.
- Fiorenza, Mariella,Mordini, Alessandro,Papaleo, Sandro,Pastorelli, Stefania,Ricci, Alfredo
-
p. 787 - 788
(2007/10/02)
-
- Carbon-Carbon Bond Formation between α-Halogenoketones and Aldehydes Promoted by Cerium(III) Iodide or Cerium(III) Chloride-Sodium Iodide
-
α-Halogenoketones react with aldehydes to form α,β-unsaturated ketones accompanied by dehalogenation in the presence of cerium(III) iodide, but the use of cerium(III) chloride-sodium iodide results in the formation of β-keto alcohols.
- Fukuzawa, Shin-ichi,Fujinami, Tatsuo,Sakai, Shizuyoshi
-
p. 777 - 778
(2007/10/02)
-
- CATALYSE HETEROGENE PAR DES SELS ET SANS SOLVANT. III. SYNTHESE DE COMPOSES CARBONYLES α,β INSATURES A PARTIR D'ETHERS D'ENOLS SILYLES
-
The reactions of silyl enol ethers with carbonyl compounds are activated by heterogeneous catalysis.Caesium fluoride is the best catalyst.Unsaturated ketones are directly obtained by condensation reactions of silyl enol ethers with aldehydes and ketones. 1,4 Addition with α,β-unsaturated carbonyl compounds gives 1,5 dicarbonyl products.This method is very convenient and the compounds obtained can easily be separated.We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.
- Boyer, J.,Corriu, R. J. P.,Perz, R.,Reye, C.
-
p. 157 - 166
(2007/10/02)
-