- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
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A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
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p. 1218 - 1220
(2019/07/16)
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- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
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The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
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- Oxidant-free thiocyanation of phenols and carbonyl compounds under solvent-free conditions by AlCl 3/NH 4SCN
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A simple, efficient, solvent-free, and mild method for thiocyanation of phenols by ammonium thiocyanate (NH4SCN) in the presence of AlCl3 has been developed. This new methodology was used to prepare para-thiocyanated products in good to excellent yields at 70°C. In addition, the successful α-thiocyanation of various ketones has also been described. Finally, a plausible mechanism of thiocyanation has been suggested.
- Nikoofar, Kobra,Gorji, Samareh
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- A 2-thiocyano HYPNONE derivatives method for the preparation of
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The invention discloses a method for preparing 2-sulfur cyano acetophenone derivatives. The method for preparing the 2-sulfur cyano acetophenone derivatives comprises the following steps: dissolving styrene derivatives and ammonium thiocyanate in a solvent, and reacting at 20-30 DEG C to obtain 2-sulfur cyano acetophenone derivatives. According to the method for preparing the 2-sulfur cyano acetophenone derivatives, the styrene derivatives are taken as starting materials; the raw materials are easily available and various in type; products prepared by the method have various in type, can be directly used and can also be used for other further reactions; meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-processing process; an accelerant does not need to be added; the production process meets the green and chemical requirements, is relatively high in yield and is suitable for large-scale production.
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Paragraph 0096-0099
(2016/10/10)
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- Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones
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A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.
- Muthyala, Manoj Kumar,Choudhary, Sunita,Kumar, Anil
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p. 14297 - 14303
(2014/04/17)
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- Fragment-based drug discovery of 2-thiazolidinones as inhibitors of the histone reader BRD4 bromodomain
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Recognizing acetyllysine of histone is a vital process of epigenetic regulation that is mediated by a protein module called bromodomain. To contribute novel scaffolds for developing into bromodomain inhibitors, we utilize a fragment-based drug discovery approach. By successively applying docking and X-ray crystallography, we were able to identify 9 fragment hits from diffracting more than 60 crystals. In the present work, we described four of them and carried out the integrated lead optimization for fragment 8, which bears a 2-thiazolidinone core. After several rounds of structure guided modifications, we assessed the druggability of 2-thiazolidinone by modulating in vitro pharmacokinetic studies and cellular activity assay. The results showed that two potent compounds of 2-thiazolidinones have good metabolic stability. Also, the cellular assay confirmed the activities of 2-thiazolidinones. Together, we hope the identified 2-thiazolidinone chemotype and other fragment hits described herein can stimulate researchers to develop more diversified bromodomain inhibitors.
- Zhao, Lele,Cao, Danyan,Chen, Tiantian,Wang, Yingqing,Miao, Zehong,Xu, Yechun,Chen, Wuyan,Wang, Xin,Li, Yanlian,Du, Zhiyan,Xiong, Bing,Li, Jian,Xu, Chunyan,Zhang, Naixia,He, Jianhua,Shen, Jingkang
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p. 3833 - 3851
(2013/07/11)
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- Synthesis, characterization and application of β-cyclodextrin-silica nanocomposite as potential microvessel in nucleophilic substitution reaction of phenacyl halides
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In the present study, β-cyclodextrin-silica hybrid is synthesized as a novel, efficient and eco-friendly microvessel and solid-liquid phase-transfer catalyst. This molecular host system was applied for nucleophilic substitution reaction of phenacyl halide
- Kiasat, Ali Reza,Nazari, Simin
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p. 429 - 438
(2014/01/06)
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- Inhibitory effect of 4-aryl 2-substituted aniline-thiazole analogs on growth of human prostate cancer LNCap cells
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Androgen receptor (AR) is ligand-inducible nuclear hormone receptor which has been focused on key molecular target in growth and progression of prostate cancer. We synthesized a series of 4-aryl 2-substituted aniline-thiazole analogs and evaluated their anti-cancer activity in AR-dependent human prostate cancer LNCap cells. Among them, the compound 6 inhibited the tumor growth in LNCap-inoculated xenograft model.
- Baek, Seung-Hwa,Kim, Nakjeong,Kim, Seong Hwan,Park, Kwang Hwa,Jeong, Kyung-Chae,Park, Bae Keun,Kang, Nam Sook
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scheme or table
p. 111 - 114
(2012/03/26)
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- A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
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A very rapid, convenient, and general method for the synthesis of α-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl α-halo carbonyls, β-keto tosylates, α-halo β-dicarbonyl, α-tosyl, β-dicarbonyl, alkyl halide, and alkyl tosylates.
- Meshram,Thakur, Pramod B.,Madhu Babu,Bangade, Vikas M.
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experimental part
p. 1780 - 1785
(2012/05/04)
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- Efficient α-thiocyanation of ketones using pyridinium hydrobromide perbromide
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The direct α-thiocyanation of ketones with ammonium thiocyanate has been achieved using pyridinium hydrobromide perbromide under mild and neutral conditions to produce α-ketothiocyanates in excellent yields and with high selectivity. Copyright
- Wu, Liqiang,Yang, Xiaojuan
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experimental part
p. 748 - 753
(2012/06/18)
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- β-cyclodextrin immobilized onto dowex resin: A unique microvessel and heterogeneous catalyst in nucleophilic substitution reactions
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The catalytic activity of β-cyclodextrin immobilized on Dowex resin as an efficient solid-liquid phase transfer catalyst was developed for the synthesis of alkyl thiocyanates and phenacyl derivatives in water. The nucleophilic substitution reactions were performed under mild reaction condition and gave the products in excellent yields. Furthermore, the catalyst could be recycled by facile separation without any loss of activity.
- Kiasat, Ali Reza,Zarinderakht, Nasrollah,Sayyahi, Soheil
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experimental part
p. 699 - 702
(2012/05/05)
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- Cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient reagent for the synthesis of phenacyl thiocyanates and phenacyl azides
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Styrenes efficiently undergo thiocyanation and azidation with cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate at 0C to furnish the corresponding thiocyanatoketones and azidoketones. This method is a direct, one-pot synthesis under mild condition using methanol as solvent.
- Badri, Rashid,Gorjizadeh, Maryam
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experimental part
p. 2058 - 2066
(2012/06/04)
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- Selectfluor: A novel and efficient reagent for the rapid α-thiocyanation of ketones
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The direct α-thiocyanation of ketones with ammonium thiocyanate has been achieved using Selectfluor under mild and neutral conditions to produce α-ketothiocyanates, in excellent yields and with high selectivity.
- Wu, Dezhen,Yang, Xiaojuan,Wu, Liqiang
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p. 901 - 905,5
(2020/09/09)
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- An efficient method for synthesis of phenacyl derivatives under homogeneous phase transfer catalyst condition in aqueous media
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In this letter, a mild and efficient procedure for synthesis of phenacyl derivatives under homogenous catalysis in the presence of tetrabutylammonium bromide in aqueous media is described. The nucleophilic substitution reactions were performed under ecofriendly conditions and gave the corresponding products in high yields and short reaction times.
- Sayyahi, Soheil,Saghanezhad, Jafar
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experimental part
p. 300 - 302
(2012/01/14)
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- I2O5 as a mild, inexpensive, and environmentally benign oxidant for the α-thiocyanation of ketones
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-Thiocyanation of various ketones has been achieved using ammonium thiocyanate as a thiocyanation reagent and I2O5 as an oxidant in methanol solution at room temperature. Figure Presented.
- Wu, Liqiang,Yang, Xiaojuan,Yan, Fulin
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experimental part
p. 105 - 110
(2012/01/06)
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- NBS or DEAD as effective reagents in α-thiocyanation of enolizable ketones with ammonium thiocyanate
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Ketones possessing α-hydrogen undergo smooth thiocyanation with ammonium thiocyanate in the presence of N-bromosuccinimide (NBS) at room temperature in acetonitrile under neutral conditions to produce the corresponding α-ketothiocyanates in excellent yiel
- Reddy, B.V. Subba,Reddy, S. Madhu Sudana,Madan, Ch.
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experimental part
p. 1432 - 1435
(2011/06/10)
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- Mild and efficient method for-thiocyanation of ketones and-dicarbonyl compounds using bromodimethylsulfonium bromide-ammonium thiocyanate
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An efficient and convenient method for-thiocyanation of ketones and-dicarbonyl compounds has been developed using a reagent combination of bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate in acetonitrile. The developed method is mild and gave good yield of the products at room temperature.
- Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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experimental part
p. 799 - 807
(2010/05/17)
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- seco-Cyclothialidines: New concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties
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seco-Cyclothialidines are a promising class of bacterial DNA gyrase B subunit inhibitors. A new seco-cyclothialidine derivative containing a dioxazine moiety, BAY 50-7952, was synthesized through a new concise pathway. One key step of the synthesis is the
- Rudolph,Theis,Hanke,Endermann,Johannsen,Geschke
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p. 619 - 626
(2007/10/03)
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- Facile access to N-thiazolyl α-amino acids from α-bromo ketones and α-amino acids
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N-Substituted 2-aminothiazoles are synthesized in a one-pot procedure using readily available α-bromo ketones and amines. This method is compatible with a wide range of functional groups and offers a facile and efficient access to the class of N-thiazolyl
- Rudolph, Joachim
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p. 3161 - 3165
(2007/10/03)
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- Reaction of 4-Aryl-2-hydrazinothiazoles with Ethyl Acetoacetate: A Reinvestigation
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The reaction of 4-aryl-2-hydrazinothiazoles (1a,b) with ethyl acetoacetate (2) affords 1-(4'-aryl 2'-thiazolyl)-3-methylpyrazol-5-ols (3a,b) rather than 3-arylthiazolotriazepin-5-ones (4a,b),as previously reported.The correct structural assignment is based on an alternate synthesis involving reaction of phenacyl bromides (6) and 3-methylpyrazol-5-ol-1-thiocarboxamide (7).The keto/enol tautomerism of 3 has been investigated using PMR spectroscopy.
- Singh, S. P.,Sehgal, Subhash,Diwakar, P.,Vaid, R. K.
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p. 573 - 575
(2007/10/02)
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