- An ionic liquid supported on magnetite nanoparticles as an efficient heterogeneous catalyst for the synthesis of alkyl thiocyanates in water
-
The present study describes a convenient method to synthesize alkyl thiocyanates from alkyl halides with the use of a novel nanomagnetic-supported organocatalyst (MNP@PEG-ImCl). The new supported ionic liquid is fully characterized by field-emission scanning electron microscopy (FESEM), Fourier-transform infrared (FT-IR), energy dispersive X-ray analysis (EDAX), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM) as well as thermogravimetric analysis (TGA) techniques. It is noteworthy that we observed easy separation of the catalyst from the reaction mixture by a simple magnetic decantation and its reutilization many times without any appreciable loss of activities.
- Fallah-Mehrjardi, Mehdi,Sayyahi, Soheil
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p. 335 - 345
(2021/02/26)
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- Visible-Light-Mediated Additive-Free Decarboxylative Ketonization Reaction of Acrylic Acids: An Access to α-Thiocyanate Ketones
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Visible-light-mediated additive-free decarboxylative functionalization of acrylic acids has been developed. The reaction uses inexpensive organic dye 9,10-dicyanoanthracene as a photocatalyst and uses the ubiquitous dioxygen as both an oxygen source and an oxidant. Through this mild and environmentally friendly method, a series of important α-thiocyanate ketones can be generated from easily available acrylic acids and ammonium thiocyanate. In addition, the facile transformation of product α-thiocyanate ketones makes this method have great potential for application in organic and pharmaceutical chemistry.
- Wang, Zhi-Lv,Chen, Jie,He, Yan-Hong,Guan, Zhi
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p. 3741 - 3749
(2021/03/09)
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- Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides
-
Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a metal-free heterogeneous photocatalyst for thiocyanation transformations. The reaction proceeds efficiently by utilizing air as a green oxidant under mild reaction conditions, which affords SCN-containing compounds in moderate to excellent yields. Meanwhile, the practicality of this protocol is further demonstrated by the reusability of the mpg-C3N4photocatalyst and the scaled-up reaction. Furthermore, detailed mechanistic studies clearly demonstrate the role of oxygen.
- Chen, Wei,Li, Tingzhen,Peng, Xinwen
-
supporting information
p. 14058 - 14062
(2021/08/16)
-
- Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands
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A family of three spatially directional resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- A nd environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic solvents. The recoverability and reusability of RCG catalytic systems, that is, RCG1 and RCG3, were also examined upon a simple extraction of the desired products using DCM or ethyl acetate, followed by subjecting the recovered aqueous solution containing the RCG catalysts to the next reaction cycles.
- Husain, Ali A.,Bisht, Kirpal S.
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p. 9928 - 9935
(2020/09/03)
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- Photo-sensitized oxy-thiocyanation of terminal alkynes/1,3-aryldienes and their one-pot conversion to 2-hydroxy 4-substituted aryl thiazoles
-
A regioselective visible light induced synthesis of aryl α-thiocyano ketones/thiocyano alcohols from activated terminal aryl alkynes and aryl 1,3-conjugated dienes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air in the presence of an organic photo-catalyst and NH4SCN. This protocol was also demonstrated at the 5 mmol scale for the synthesis of potentially therapeutic 2-hydroxy 4-substituted arylthiazoles in good yields, signifying its amenability for large-scale application.
- Gullapalli, Kumaraswamy,Vijaykumar, Swargam
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p. 2232 - 2241
(2019/02/27)
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- 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
-
p. 1218 - 1220
(2019/07/16)
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- Ag-Catalyzed Thiocyanofunctionalization of Terminal Alkynes to Access Alkynylthiocyanates and α-Thiocyanoketones
-
Unprecedented one-pot thiocyanofunctionalizations of terminal alkynes to deliver alkynylthiocyanates and α-thiocyanoketones using a silver-catalyzed procedure or under silver/gold relay catalysis is reported. These synthetically valuable organothiocyanates are accessed in high efficiency, and their derivatization into a variety of valuable sulfur-containing heterocycles and sulfides has also been demonstrated.
- See, Jie Yang,Zhao, Yu
-
supporting information
p. 7433 - 7436
(2018/12/11)
-
- Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones
-
A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C-S and C=O bonds simply by using nontoxic and inexpensive Na 2 -Eosin Y as a photocatalyst.
- Nan, Guangming,Yue, Huilan
-
supporting information
p. 1340 - 1345
(2018/05/03)
-
- N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications
-
N-Thiocyanatosaccharin (R1) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.
- Wu, Di,Qiu, Jiashen,Karmaker, Pran Gopal,Yin, Hongquan,Chen, Fu-Xue
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p. 1576 - 1583
(2018/02/09)
-
- Ammonium [11C]thiocyanate: revised preparation and reactivity studies of a versatile nucleophile for carbon-11 radiolabelling
-
Herein we report the preparation of ammonium [11C]thiocyanate via the reaction of [11C]CS2 with ammonia. The [11C]SCN- ion is demonstrated as a potent nucleophile that can be used to readily generate a range of 11C-labelled thiocyanate molecules in high conversions. Furthermore, novel 11C-labelled thiazolone molecules can be easily prepared from the intermediate α-thiocyanatophenones via an acid mediated cyclisation reaction.
- Haywood, Tom,Cesarec, Sara,Kealey, Steven,Plisson, Christophe,Miller, Philip W.
-
supporting information
p. 1311 - 1314
(2018/08/28)
-
- One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
-
An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.
- Xu, Lijun,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
-
supporting information
p. 6057 - 6066
(2017/09/23)
-
- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
-
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
-
-
- Oxidant-free thiocyanation of phenols and carbonyl compounds under solvent-free conditions by AlCl 3/NH 4SCN
-
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
-
-
- Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones
-
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
-
p. 14297 - 14303
(2014/04/17)
-
- A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
-
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.
-
experimental part
p. 1780 - 1785
(2012/05/04)
-
- β-cyclodextrin immobilized onto dowex resin: A unique microvessel and heterogeneous catalyst in nucleophilic substitution reactions
-
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
-
experimental part
p. 699 - 702
(2012/05/05)
-
- Selectfluor: A novel and efficient reagent for the rapid α-thiocyanation of ketones
-
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
-
p. 901 - 905,5
(2020/09/09)
-
- Cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient reagent for the synthesis of phenacyl thiocyanates and phenacyl azides
-
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
-
experimental part
p. 2058 - 2066
(2012/06/04)
-
- Efficient α-thiocyanation of ketones using pyridinium hydrobromide perbromide
-
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
-
experimental part
p. 748 - 753
(2012/06/18)
-
- A novel and efficient synthesis of alkyl thiocyanates from alkyl halides in water using phase transfer catalysts
-
1,4-Bis(triphenylphosphonium)-2-butene dichloride (BTPBDC) and 1,4-bis(triphenyl phosphonium)-2-butene dithiocyanate (BTPBDT) were prepared and used as phase-transfer catalysts. Alkyl halides were converted efficiently to the corresponding alkyl thiocyanates under mild reaction conditions in water. No evidence for the formation of isothiocyanates as by-product of the reaction was observed.
- Gorjizadeh, Maryam,Sayyahi, Soheil
-
experimental part
p. 659 - 662
(2012/01/05)
-
- An efficient method for synthesis of phenacyl derivatives under homogeneous phase transfer catalyst condition in aqueous media
-
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
-
experimental part
p. 300 - 302
(2012/01/14)
-
- I2O5 as a mild, inexpensive, and environmentally benign oxidant for the α-thiocyanation of ketones
-
-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
-
experimental part
p. 105 - 110
(2012/01/06)
-
- Mild and efficient method for-thiocyanation of ketones and-dicarbonyl compounds using bromodimethylsulfonium bromide-ammonium thiocyanate
-
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.
-
experimental part
p. 799 - 807
(2010/05/17)
-
- A simple and efficient thiocyanation of indoles, anilines and keto compounds catalyzed by a polystyrene resin amberlyst-15
-
Thiocyanation of various aromatic, heteroaromatic and enolizable ketone compounds has been achieved with ammonium thiocyanate in presence of polystyrene cation exchange resin, Amberlyst-15. All the reactions were carried out in acetonitrile at room temper
- Lenin, Racha,Raju, Rallabandi M.
-
experimental part
p. 392 - 395
(2011/04/12)
-
- Heteropoly acids as heterogeneous and reusable catalyst for α-thiocyanation of ketones
-
Simple, efficient, and mild method for -thiocyanation of ketones in presence of heteropolyacid has been developed. This methodology offered -oxothiocyanates in good to excellent yields at room temperature in a highly selective manner. The catalyst could b
- Chaskar, Atul C.,Yadav, Arun A.,Langi, Bhushan P.,Murugappan, Anita,Shah, Chetan
-
experimental part
p. 2850 - 2856
(2010/10/20)
-
- Acyl-isothiocyanates as efficient thiocyanate transfer reagents
-
An unprecedented transfer of a thiocyanate (-SCN) group from aroyl/acyl isothiocyanate to alkyl or benzylic bromide is observed in the presence of a tertiary amine. This process is most effective when the bromomethyl proton is less acidic, while the prese
- Palsuledesai, Charuta C.,Murru, Siva,Sahoo, Santosh K.,Patel, Bhisma K.
-
supporting information; experimental part
p. 3382 - 3385
(2009/12/01)
-
- Hypervalent iodine(III) sulfonate mediated synthesis of α-thiocynanatoketones in a task-specific ionic liquid [bmim]SCN
-
The task-specific ionic liquid (TSIL) and 1-n-butyl-3-methylimidazolium thiocynanate, ([bmim]SCN) were used as the medium as well as the reactant for the synthesis of α-thiocynanatoketones by the reaction with α-sulfonyloxy aryl ketones. Significant rate enhancements and improved yields have been observed.
- Huang, Hsin-Yu,Wang, Huey-Min,Hou, Rei-Sheu,Cheng, Hui-Ting,Chen, Ling-Ching
-
experimental part
p. 1204 - 1207
(2009/12/03)
-
- Direct α-thiocyanation of carbonyl and β-dicarbonyl compounds using potassium peroxydisulfate-copper(II)
-
A convenient approach for the direct α-thiocyanation of carbonyl and β-dicarbonyl compounds has been developed using ammonium thiocyanate as the thiocyanating agent and potassium peroxydisulfate as the oxidant in the presence of a catalytic amount of copp
- Kumar, Atul,Ahamd,Maurya
-
p. 1399 - 1401
(2007/10/03)
-
- A task-specific ionic liquid [bmim]SCN for the conversion of alkyl halides to alkyl thiocyanates at room temperature
-
A new task-specific ionic liquid (TSIL), 1-n-butyl-3- methylimidazolium thiocyanate ([bmim]SCN), has been prepared and used for the first time as the medium as well as reactant for the synthesis of alkyl thiocyanates from the corresponding alkyl halides by thiocyanate-halide exchange at room temperature. The alkyl thiocyanate products can be easily isolated from the reaction mixture by simple extraction and the ionic liquid 1-n-butyl-3-methylimidazolium halide may be reused for the synthesis of the ionic liquid [bmim]SCN and recycled for further use.
- Kamal, Ahmed,Chouhan, Gagan
-
p. 1489 - 1491
(2007/10/03)
-
- New heteroarylbenzenesulphonamides as matrix metalloproteinase inhibitors
-
A series of derivatives of 2,4- and 2,5-thiazolyl- or oxazolylbenzenesulphonamides has been prepared and evaluated as potential MMP inhibitors. The thiazole 15b have been found to exhibit MMP-2 and MMP-9 inhibitions higher than reference compounds GI 129471 and CGS 27023A.
- Delbecq, Frederic,Cordonnier, Guy,Pommery, Nicole,Barbry, Didier,Henichart, Jean-Pierre
-
p. 1119 - 1121
(2007/10/03)
-
- A novel and efficient method for the synthesis of α-azidoketones and α-ketothiocyanates
-
α-Diazoketones underwent insertion smoothly with sodium azide and potassium thiocyanate in the presence of CeCl3 ·7H 2O under mild reaction conditions to afford the corresponding α-azidoketones and α-ketothiocyanates in excellent yields.
- Yadav,Subba Reddy,Srinivas
-
p. 882 - 883
(2007/10/03)
-
- Cerium(IV) ammonium nitrate mediated addition of thiocyanate and azide to styrenes: Expeditious routes to phenacyl thiocyanates and phenacyl azides
-
An efficient synthesis of phenacyl thiocyanates and phenacyl azides is described here. Styrenes react with ammonium thiocyanate and sodium azide in the presence of cerium(IV) ammonium nitrate under an oxygen atmosphere to afford phenacyl thiocyanates and phenacyl azides respectively in good yields. (C) 2000 Published by Elsevier Science Ltd.
- Nair, Vijay,Nair, Latha G,George, Tesmol G,Augustine, Anu
-
p. 7607 - 7611
(2007/10/03)
-
- Synthesis and solvatochromic properties of 5-dicyanovinyl- and 5-tricyanovinyl-substituted 2-amino-thiazoles and 2-amino-thiophenes
-
Starting from 2-morpholinothiazoles 6 and 2-morpholinothiophenes 7 and following known routes several 5-dicyanovinyl and 5-tricyanovinyl-substituted derivatives 10 - 13 have been prepared and their solvatochromic properties estimated.
- Eckert, Katrin,Mokry, Cornelia,Schroeder, Anke,Hartmann, Horst
-
-
- Hypervalent iodine in organic synthesis: One pot facile syntheses of α-thiocyanatoacetophenones, 2-hydroxy-, and 2-mercapto-4-arylthiazoles using [hydroxy (tosyloxy)iodo]benzene
-
Hypervalent iodine oxidation of acetophenones (1a-1e) with [hydroxy(tosyloxy)iodo]benze, followed by treatment with potassium thiocyanate offers a new facile synthesis of corresponding α-thiocyanatoacetophenones (3a-3e). Cyclization of 3a-3e, thus generated in situ, using AcOH/H2O and H2NC(S)NH2/HCl provides one pot facile syntheses of 2-hydroxy-, and 2-mercapto-4-arylthiazoles (4 and 5) respectively.
- Prakash,Saini
-
p. 1455 - 1462
(2007/10/02)
-