- A task-specific ionic liquid [bmim]SCN for the conversion of alkyl halides to alkyl thiocyanates at room temperature
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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
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Read Online
- Photo-sensitized oxy-thiocyanation of terminal alkynes/1,3-aryldienes and their one-pot conversion to 2-hydroxy 4-substituted aryl thiazoles
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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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Read Online
- α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen
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A facile method is disclosed for the synthesis of α-thio/selenocyanato ketones through regioselective C-H thio/selenocyanation of ketones. The advantages include the use of easily available starting materials, high efficiency, simple operation, and easy scale-up. Control experiments provide evidence that the reaction proceeded via a radical way, while kinetic isotope effect experiments reveal that the cleavage of the C-H bond serves as the rate-limiting step.
- Li, Jin-Cheng,Gao, Wen-Xia,Liu, Miao-Chang,Zhou, Yun-Bing,Wu, Hua-Yue
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p. 17294 - 17306
(2021/12/02)
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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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- Boron-doped TiO2(B-TiO2): visible-light photocatalytic difunctionalization of alkenes and alkynes
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Boron-doped TiO2(B-TiO2) was prepared, characterized, and successfully applied as a reusable, inexpensive, available, and heterogeneous nanophotocatalyst under visible light for a novel method of construction of phenacyl thiocyanate compounds from double or triple bonds. Impressive aspects of this project are obtaining the desired compounds in a short time, using a renewable energy source, and using a catalyst with easy extraction that is solvent-safe, and without the use of any oxidants, bases, and ligands, or harsh conditions. This is the first report of the construction of phenacyl thiocyanates through this photocatalytic method under visible light.
- Hosseini-Sarvari, Mona,Valikhani, Atefe
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supporting information
p. 12464 - 12470
(2021/07/25)
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- Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides
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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
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supporting information
p. 14058 - 14062
(2021/08/16)
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- Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones
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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
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supporting information
p. 1340 - 1345
(2018/05/03)
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- Ammonium [11C]thiocyanate: revised preparation and reactivity studies of a versatile nucleophile for carbon-11 radiolabelling
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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.
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supporting information
p. 1311 - 1314
(2018/08/28)
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- Compound
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Provided are a compound indicated as formula (A-I), a coloring hardening resin composition including the compound, a color filter formed using the resin composition and a display including the color filter. In formula (A-I), X refers to an oxygen atom, a nitrogen atom or a sulfur atom. ′Y′^(m-) refers to any m-valent anion. R^41-R^46 independently refer to a hydrogen atom and an alkyl group having 1-20 carbons capable of being replaced with an amino group or a halogen atom. R^47-R^54 independently refer to a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, or an alkyl group having 1-8 carbons. R^55 refers to a hydrogen atom, an alkyl group having 1-20 carbons, or an aryl group capable of being replaced.
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Paragraph 0258
(2017/06/02)
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- One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
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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
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supporting information
p. 6057 - 6066
(2017/09/23)
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- Colored dispersion
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PROBLEM TO BE SOLVED: To provide a colored dispersion comprising a colorant for color filters having improved heat resistance. SOLUTION: A colored dispersion comprises a compound represented by formula (A-I) and solvent [X is O or S; R41-R46 are H, a saturated hydrocarbon group or the like; R47-R54 are H, a halogen atom, an alkyl group or the like; R55 is H, an aryl group or the like; [Y]m- is an m-valent anion comprising at least one element selected from tungsten, molybdenum, silicon, and phosphorus, and oxygen as essential elements]. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0247; 0248
(2016/11/09)
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- MUTANT IDH1 INHIBITORS USEFUL FOR TREATING CANCER
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Compounds of Formula I and Formula II and the pharmaceutically acceptable salts thereof are disclosed The variables A, B, Y, Z, X1, X2, R1-4 and R13-18 are disclosed herein. The compounds are useful for treating cancer disorders, especially those involving mutant IDH1 enzymes. Pharmaceutical compositions containing compounds of Formula I or Formula II and methods of treatment comprising administering compounds of Formula I and Formula II are also disclosed.
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Paragraph 0240
(2016/07/27)
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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 0076-0079
(2016/10/10)
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- COLORED CURABLE RESIN COMPOSITION
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The present invention provides a colored curable resin composition capable of enhancing the heat resistance of a color filter. The present invention provides a colored curable resin composition comprising a dye (A1) consisting of an ion represented by chemical formula (A-VI) and a counter ion, resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E); and at least one dye (A2) selected from the group consisting of an anthraquinone dye and a tetraazaporphyrin dye, a colorless metal complex (F), or both the dye (A2) and the metal complex (F).COPYRIGHT KIPO 2015
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Paragraph 0729-0731
(2016/11/28)
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- Molecular oxygen induced free radical oxythiocyanation of styrenes leading to α-oxothiocyanates
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A facile and efficient protocol of oxythiocyanation of styrenes with ammonium thiocyanate has been developed. The reaction proceeded at room temperature using oxygen as sole oxidant to afford the α-oxothiocyanates via radical pathway in moderate to good yields. This method is straightforward, green and cost-effective, requires no catalyst and additives.
- Liu, Kui,Li, Da-Peng,Zhou, Shao-Fang,Pan, Xiang-Qiang,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
p. 4031 - 4034
(2015/06/02)
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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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- 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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- 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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- 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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- 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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- One-pot tandem copper-catalyzed library synthesis of 1-thiazolyl-1,2,3- triazoles as anticancer agents
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One-pot multicomponent synthesis to assemble compounds has been an efficient method for constructing a compound library. We have developed one-pot tandem copper-catalyzed azidation and CuAAC reactions that afford 1-thiazolyl-1,2,3-triazoles with anticancer activity. By utilizing this one-pot synthetic strategy, we constructed a library of 1-thiazolyl-1,2,3-triazoles in search of the potent lead compound. Furthermore, 1-thiazolyl-1,2,3-triazoles were evaluated for anticancer activity against the multidrug-resistant cancer cells MES-SA/Dx5. Most of the 1-thiazolyl-1,2,3-triazoles revealed cytotoxic effect against cancer cells at micromolar to low micromolar range. Testing some of the most potent compounds (5{4,2-4} and 5{5,1-3}) against the normal cell line Vero showed no significant toxicity (except 5{4,2}) to normal cells. This result indicates that compounds 5{4,3-4} and 5{5,1-3} possessed good potency and selectivity to cancer cells over normal cells.
- Li, Wen-Tai,Wu, Wan-Hsun,Tang, Chien-Hsiang,Tai, Ready,Chen, Shui-Tein
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scheme or table
p. 72 - 78
(2011/04/17)
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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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- 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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- Simple and quick preparation of α-thiocyanate ketones in hydroalcoholic media. Access to 5-aryl-2-imino-1,3-oxathiolanes
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A simple preparation on gram-scale of thiocyanate derivatives via nucleophilic substitution of halogenated compounds with SCN salts at high substrate concentrations in a few minutes and excellent yields was successfully accomplished in hydroalcoholic media. The obtained compounds were employed for the efficient synthesis of valuable 5-aryl-2-imino-1,3-oxathiolane derivatives (a one-pot approach is also presented).
- Bisogno, Fabricio R.,Cuetos, Anibal,Lavandera, Ivan,Gotor, Vicente
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supporting information; experimental part
p. 452 - 454
(2010/04/22)
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- Hypervalent iodine(III) sulfonate mediated synthesis of α-thiocynanatoketones in a task-specific ionic liquid [bmim]SCN
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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
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experimental part
p. 1204 - 1207
(2009/12/03)
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- MODULATORS OF AMYLOID BETA
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The invention relates to compounds of formula wherein hetaryl I, hetaryl II, and R1 are as described herein. Compounds of formula I are modulators for amyloid beta and thus, they may be useful for the treatment or prevention of a disease associated with the deposition of β-amyloid in the brain, in particular Alzheimer's disease.
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Page/Page column 12
(2011/07/06)
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- SUBSTITUTED THIAZOLE DERIVATIVES BEARING 3-PYRIDYL GROUPS, PROCESS FOR PREPARING THE SAME AND USE THEREOF
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The present invention provides a pharmaceutical composition having a steroid C17,20-lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism, tumor such as breast cancer and the like, more particularly, a steroid C17,20-lyase inhibitor containing a compound represented by the formula: wherein A1 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, one of A2 and A3 is a hydrogen atom, a halogen atom, a C1-4 aliphatic hydrocarbon group optionally having substituents or an optionally esterified carboxyl group, the other of A2 and A3 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, and at least one of A1, A2 and A3 is a 3-pyridyl group optionally having substituents, or a salt thereof or a prodrug thereof.
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Page/Page column 40
(2008/06/13)
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- Cerium(IV) ammonium nitrate mediated addition of thiocyanate and azide to styrenes: Expeditious routes to phenacyl thiocyanates and phenacyl azides
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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
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p. 7607 - 7611
(2007/10/03)
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- Hypervalent iodine oxidation: A facile access to α-thiocyanatoketones
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Aryl alkyl ketones (1) on treatment with benzene or benzene undergo oxidation via α-sulphonyloxyketones as intermediates to form α-thiocyanoketones (2) in excellent yields.
- Khanna, Mahavir S.,Sangeeta,Garg, Chandra P.,Kapoor, Ram P.
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- Hypervalent iodine in organic synthesis: One pot facile syntheses of α-thiocyanatoacetophenones, 2-hydroxy-, and 2-mercapto-4-arylthiazoles using [hydroxy (tosyloxy)iodo]benzene
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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
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p. 1455 - 1462
(2007/10/02)
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- Unexpected Formation of α-Thiocyanatoketones in Hantzsch Thiazole Synthesis
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The reaction of 3,5-dimethylpyrazole-1-thiocarboxamide (3) with α-haloketones (4) yields the corresponding α-thiocyanatoketones (5) or pyrazoles (1) depending upon nature of the halogen.Many such pyrazole derivatives have erroneously been described as thiazolotriazepines in literature.
- Singh, S. P.,Sehgal, Subhash,Singh, Lukhvinder,Dhawan, S. N.
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p. 154 - 155
(2007/10/02)
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