- N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity
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A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.
- Li, Chengqiu,Long, Pingliang,Wu, Haopeng,Yin, Hongquan,Chen, Fu-Xue
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supporting information
p. 7131 - 7134
(2019/08/07)
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- Rapid and efficient thiocyanation of phenols, indoles, and anilines in 1,1,1,3,3,3-hexafluoro-2-propanol under ultrasound irradiation
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An efficient ultrasound-promoted thiocyanation of phenols, indoles, and anilines in the presence of N-chlorosuccinimide and NH4SCN using 1,1,1,3,3,3-hexafluoro-2-propanol as the solvent has been developed. The major features of the present protocol include the mild reaction conditions, short reaction times, good to excellent yields, and broad substrate scope. Moreover, scale-up synthesis can be achieved and the solvent can be easily recovered and reused.
- Wang, Zhonghao,Wang, Liang,Chen, Qun,He, Ming-yang
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supporting information
p. 76 - 84
(2017/12/28)
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- 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
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Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
- Khosravi, Kaveh,Naserifar, Shirin
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supporting information
p. 6584 - 6592
(2018/10/05)
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- N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications
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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)
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- Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
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An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct C[sbnd]H functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated in gram scale synthesis of a precursor of PPAR δ agonist in excellent yield.
- Mete, Trimbak B.,Khopade, Tushar M.,Bhat, Ramakrishna G.
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supporting information
p. 415 - 418
(2017/01/10)
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- Graphene oxide: A promising carbocatalyst for the regioselective thiocyanation of aromatic amines, phenols, anisols and enolizable ketones by hydrogen peroxide/KSCN in water
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Graphene oxide (GO), as a heterogeneous carbocatalyst, catalyzes the direct thiocyanation of a variety of arenes including aromatic amines, phenols, anisols and carbonyl compounds that possessing α-hydrogen in the presence of hydrogen peroxide and KSCN in water as a green media. This procedure is chemoselective, avoids the use of precious metals and toxic solvents and has a broad substrate scope. Easy removal from the reaction mixture and recyclability with no loss of activity are the key features of graphene oxide in this catalytic system.
- Khalili, Dariush
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p. 2547 - 2553
(2016/03/19)
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- Zeolite H-Sdusy Powder (Cbv720) as a Recyclable Catalyst for an Efficient Thiocyanation of Aromatic and Heteroaromatic Compounds in Acetonitrile
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Thiocyanation of various aromatic and heteroaromatic compounds has been studied using Zeolite H-SDUSY Powder (CBV720) as catalyst and ammonium thiocyanate (NH4SCN) as thiocyanation reagent in acetonitrile medium. Reactions afforded good yields of products under stirred conditions at reflux temperature. Reactions underwent enhancements under sonication (using an ultrasonic probe of 24 kHz frequency) and microwave irradiation. The use of ultrasound decreased the reaction times from (7-12 h) to few minutes (70-150 min). The use of microwave irradiation much more effectively enhanced the reaction rates than sonicated and conventional protocols used in this study.
- Chary, V. Sudhakar,Krishnaiah,Kumar, M. Satish,Rajanna
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p. 1146 - 1153
(2015/08/04)
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- Ammonium metavanadate/thiocyanate-triggered electrophilic thiocyanation of aromatic and heteroaromatic compounds in aqueous bisulfate and acetonitrile media
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The ammonium metavanadate/thiocyanate system is used as an efficient reagent for regioselective thiocyanation of aromatic and hetero aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted and microwave-assisted reactions. The reactions proceeded smoothly and afforded good yields of products with high regioselectivity. Longer reaction times (about 8 h) observed under conventional conditions were reduced to 0.5 h/30 min under sonication and to 90 s in the case of microwave-assisted reactions.
- Venkatesham,Rajendar Reddy,Rajanna,Veerasomaiah
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p. 606 - 612
(2015/10/19)
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- An efficient and regioselective thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine)-supported thiocyanate as a versatile reagent and potassium peroxydisulfate as a strong oxidizing agent
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A green and regioselective thiocyanation of aromatic and heteroaromatic compounds has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine)-supported thiocyanate ion, [P4-VP]SCN, as a versatile polymeric reagent and potassium persulfate as a strong oxidizing agent, under heterogeneous conditions.Various indoles, phenol and aniline derivatives, and pyrroles were transformed into their corresponding aryl thiocyanates in high to excellent yields. This procedure offers advantages such as short reaction time, simple reaction work-up, and the polymeric reagents can be regenerated and reused for several times without significant loss of their activity.
- Karimi Zarchi,Banihashemi
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p. 458 - 469
(2014/06/10)
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- COMPOUND WITH AGITATION EFFECT ON PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR , AND PREPARATION METHOD AND USE THEREOF
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The present invention provides a novel compound of formula I, which has an agitation effect on the peroxisome proliferator-activated receptor subtype δ (PPARδ), to a pharmaceutical composition comprising the compound, to a process for preparation of the compound and to use of the compound in the manufacture of a medicament for treating or preventing a disease which could be treated or prevented by activating PPARδ thereof, said disease is one or more from the group comprising metabolic syndrome, obesity, dyslipidemia, pathoglycemia, insulin resistance, senile dementia and tumors. The present invention also relates to a new intermediate used in the preparation of the novel compound and a process for preparation of the intermediate.
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Page/Page column 22
(2011/06/24)
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- COMPOUND WITH AGITATION EFFECT ON PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR. PROCESS FOR ITS PREPARATION AND USE THEREOF
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The present invention provides a novel compound of formula I, which has an agitation effect on the peroxisome proliferator-activated receptor subtype δ (PPARδ), to a pharmaceutical composition comprising the compound, to a process for preparation of the compound and to use of the compound in the manufacture of a medicament for treating or preventing a disease which could be treated or prevented by activating PPARδ thereof, said disease is one or more from the group comprising metabolic syndrome, obesity, dyslipidemia, pathoglycemia, insulin resistance, senile dementia and tumors. The present invention also relates to a new intermediate used in the preparation of the novel compound and a process for preparation of the intermediate.
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Page/Page column 14-15
(2012/01/13)
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- ARYL PYRIMIDINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USES THEREOF
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The present invention relates to a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof. Various substituents in the formula (I) are as defined in the specification. The present invention also relates to a pharmaceutical composition comprising the compound of formula (I), the preparation method of compound of formula (I), and the use of the compound for the preparation of a medicament for treating and/or preventing human peroxisome proliferators activated receptor δ (hPPARδ)-associated diseases and risk factors.
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Page/Page column 8-9
(2011/02/15)
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- ARYL PYRIMIDINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USES THEREOF
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The present invention relates to a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof. Various substituents in the formula (I) are as defined in the specification. The present invention also relates to a pharmaceutical composition comprising the compound of formula (I), the preparation method of compound of formula (I), and the use of the compound for the preparation of a medicament for treating and/or preventing human peroxisome proliferators activated receptor δ (hPPARδ) -associated diseases and risk factors.
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Page/Page column 13-14
(2010/06/11)
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- INHIBITORS OF ACETYL-COA CARBOXYLASE
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The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 61
(2010/11/17)
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- Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate
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A facile method for direct thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate is described.
- Mahajan, Ulhas S.,Akamanchi, Krishnacharya G.
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experimental part
p. 2674 - 2682
(2009/12/04)
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- Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate
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Various aromatic and heteroaromatic compounds have been efficiently thiocyanated by using a novel combination of bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate. Georg Thieme Verlag Stuttgart.
- Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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p. 2952 - 2956
(2008/03/12)
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- CONDENSED PYRAZOLE DERIVATIVES AS PPAR AGONISTS II
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The invention discloses compounds of formula (I) wherein: R is a carboxylic acid or a derivative thereof; R1 and R2 are independently H or alkyl, or together R1 and R2 form an alkylene group; L1 is a
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Page/Page column 33-34
(2010/11/26)
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- Compounds that modulate PPAR activity and methods of preparation
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This invention relates to compounds that alter PPAR activity. The invention also relates to pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing dyslipidemia, hypercholesterolemia, obesity, hyperglycemia, atherosclerosis, hypertriglyceridemia and hyperinsulinemia in a mammal. The present invention also relates to methods for making the disclosed compounds.
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- Compounds that modulate PPAR activity and methods of preparation
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This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing hyperlipidemia and hypercholesteremia in a mammal. The present invention also discloses methods for making the disclosed compounds.
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- Compounds that modulate PPAR activity and methods for their preparation
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This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing disipidemia, hypercholesteremia, obesity, eating disorders, hyperglycemia, atherosclerosis, hypertriglyceridemia, hyperinsulinemia and diabetes in a mammal as well as methods of supressing appetite and modulating leptin levels in a mammal. The present invention also discloses methods for making the disclosed compounds.
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- A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor δ
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The most potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonist GW501516 (1) was synthesized in 4 steps and 78% overall yield starting from o-cresol by using a one-pot regiocontrolled dialkylation of mercaptophenol 5 as the key
- Wei, Zhi-Liang,Kozikowski, Alan P.
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p. 9116 - 9118
(2007/10/03)
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- Novel phenolic thioethers as inhibitors of 5-lipoxygenase
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The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: STR1 wherein: R1 and R2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R3 represents CO2 H, CO2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; and the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
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- Phenolic thioethers as inhibitors of 5-lipoxygenase
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The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: STR1 wherein: R1 and R2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R3 represents CO2 H, CO2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; amd the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
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