- Desulfurizing agent for thioamides
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Thioamides treated with thionyl chloride in an ionic liquid were successfully converted into amides.
- Polushina,Zavarzin,Krayushkin,Rodionova,Yarovenko
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p. 383 - 385
(2021/03/03)
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- Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
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A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.
- Chen, Xinzhi,Ge, Xin,Jin, Hao,Qian, Chao,Zhou, Shaodong
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supporting information
p. 3403 - 3406
(2021/06/25)
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- Method for synthesizing thioamide compound from 1,2,3-thiodiazole compound and amine under catalysis of copper
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The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a thioamide compound from a 1,2,3-thiodiazole compound and amine under the catalysis of copper. The method comprises the following steps: in a protective atmosphere, taking an organic solvent as a reaction medium, reacting a 1,2,3-thiodiazole compound with an amine compound under the action of a copper salt catalyst or a copper catalyst and a phosphine ligand, and carrying out subsequent treatment to obtain the thioamide compound. According to the method, the copper salt is used as the catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the reaction takes the 1,2,3-thiodiazole compound and the amine compound as raw materials, and has the advantages that the raw materials are cheap and easy to prepare, the operation is simple and convenient, and the atom economy is high.
- -
-
Paragraph 0168-0174
(2021/05/12)
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- Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)
-
For many years now, targeting deregulation within cancer cells’ metabolism has appeared as a promising strategy for the development of more specific and efficient cancer treatments. Recently, numerous reports highlighted the crucial role of the serine synthetic pathway, and particularly of the phosphoglycerate dehydrogenase (PHGDH), the first enzyme of the pathway, to sustain cancer progression. Yet, because of very weak potencies usually in cell-based settings, the inhibitors reported so far failed to lay ground on the potential of this approach. In this paper, we report a structure–activity relationship study of a series of α-ketothioamides that we have recently identified. Interestingly, this study led to a deeper understanding of the structure–activity relationship (SAR) in this series and to the identification of new PHGDH inhibitors. The activity of the more potent compounds was confirmed by cellular thermal shift assays and in cell-based experiments. We hope that this research will eventually provide a new entry point, based on this promising chemical scaffold, for the development of therapeutic agents targeting PHGDH.
- Spillier, Quentin,Ravez, Séverine,Unterlass, Judith,Corbet, Cyril,Degavre, Charline,Feron, Olivier,Frédérick, Rapha?l
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- Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S8 and Amides Leading to Aryl Thioamides
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A novel transition-metal-free cleavage reaction of C-C triple bonds in aromatic alkynes with S8 and amides furnishes aryl thioamides in moderate to excellent yields. The remarkable features of this thioamidation include the metal-free cleavage of C-C triple bond, mild reaction conditions, as well as wide substrate scope that is particularly compatible with some internal aromatic alkynes and acetamides.
- Xu, Kai,Li, Ziyi,Cheng, Fangyuan,Zuo, Zhenzhen,Wang, Tao,Wang, Mincan,Liu, Lantao
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supporting information
p. 2228 - 2231
(2018/04/30)
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- Rapid and efficient protocol for Willgerodt–Kindler’s thioacetamides catalyzed by sulfated polyborate
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Abstract: A simple and efficient method for the synthesis of one-pot, three-component thioacetamides via Willgerodt–Kindler reaction was developed using a sulfated polyborate catalyst. The method described the reaction of ketones, sulfur, and secondary am
- Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
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p. 2091 - 2095
(2017/10/06)
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- Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis
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An efficient aqueous synthesis of thioamides through aldehydes, sodium sulfide, and N-substituted formamides has been developed. Both alkyl and aryl aldehydes are amenable to this protocol. N-Substituted formamides are essential for this transformation. Readily available inorganic salt (sodium sulfide) serves as the sulfur source in water, which makes this method much more practical and efficient. Furthermore, the late-stage modification of bioactive molecules and derivatives through this protocol has been established.
- Wei, Jianpeng,Li, Yiming,Jiang, Xuefeng
-
supporting information
p. 340 - 343
(2016/02/03)
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- Synthesis of thioamides via one-pot A3-coupling of alkynyl bromides, amines, and sodium sulfide
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We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na 2S·9H2O. The developed method is applicable for a wide range of amines and alkynyl bromides bearing different functional groups furnishing the corresponding products in moderate to excellent yields. The Royal Society of Chemistry.
- Sun, Yadong,Jiang, Huanfeng,Wu, Wanqing,Zeng, Wei,Li, Jianxiao
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supporting information
p. 700 - 707
(2014/01/06)
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- Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides
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A new decarboxylative strategy has been developed for the synthesis of thioamides via a three-component reaction involving arylacetic or cinnamic acids, amines and elemental sulfur powder, without the need of a transition metal and an external oxidant.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
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supporting information
p. 3624 - 3627
(2014/08/05)
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- A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
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A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
- Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
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p. 2164 - 2170
(2013/05/08)
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- Efficient and selective multicomponent oxidative coupling of two different aliphatic primary amines into thioamides by elemental sulfur
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An efficient and selective multicomponent oxidative coupling of two different aliphatic primary amines into thioamides by elemental sulfur under solvent-free conditions has been developed.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information; experimental part
p. 4274 - 4277
(2012/09/22)
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- Sulfated tungstate: A green catalyst for synthesis of thiomorpholides via Willgerodt-Kindler reaction
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Use of sulfated tungstate as an efficient, green and reusable catalyst for preparation of thiomorpholides via Willgerodt-Kindler reaction pathway is presented. The reaction proceeds under solvent free condition. The advantages of this method are high yiel
- Salim, Suresh D.,Pathare, Sagar P.,Akamanchi, Krishnacharya G.
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experimental part
p. 78 - 81
(2012/06/04)
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- Ultrasound-mediated willgerodt-kindler reactions: Non-thermal synthesis of thioacetamides
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Non-thermal, solvent-free condensation of several aryl methyl ketones with amines and elemental sulfur is efficiently conducted using ultrasonic irradiation within short time periods. Consequently, various thioacetamides are conveniently synthesized. Simi
- Mojtahedi, Mohammad M.,Alishiri, Tooba,Abaee, M. Saeed
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experimental part
p. 1910 - 1915
(2011/10/08)
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- Silica-supported fluoroboric acid (HBF4-SiO2) catalyzed highly productive synthesis of thiomorpholides as activators of l-asparaginase as well as the antioxidant agent
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An efficient solvent-free procedure for the synthesis of thiomorpholides in the presence of a catalytic amount of solid-supported fluoroboric acid (HBF4-SiO2) is described. The advantages of this method are high yields, short reaction times, ease of product isolation, low cost, and the catalyst can be recycled for a number of times without significant loss of activity. Three thiomorpholides possessing electron-donating group (4c, 4g, and 4h) were exhibiting excellent stimulatory activities against Erwinia carotovora l-asparaginase. The most potent activator, compound 4h displayed the following kinetic parameters, Km = 75 μM and Vmax = 1000 μmol mg-1 min-1 and KA = 0.985 μM. Furthermore, these compounds (4g, 4h, 4c, 4f, 4a, and 4d) have also shown promising 2,2′-diphenyl-1-picrylhydrazyl (DPPH) reducing antioxidant activity (21-36%) at 1 mM concentration as compared to standard butylated hydroxyl anisole (72% at 1 mM).
- Bandgar, Babasaheb P.,Gawande, Shrikant S.,Warangkar, Suchita C.,Totre, Jalinder V.
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experimental part
p. 3618 - 3624
(2010/08/03)
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- Design, synthesis and evaluation of novel 2-thiophen-5-yl-3H-quinazolin-4-one analogues as inhibitors of transcription factors NF-k{cyrillic}B and AP-1 mediated transcriptional activation: Their possible utilization as anti-inflammatory and anti-cancer ag
-
In an attempt to discover novel inhibitors of NF-κB and AP-1 mediated transcriptional activation utilizing the concept of chemical lead based medicinal chemistry and bioisosterism a series of 2-(2,3-disubstituted-thiophen-5-yl)-3H-quinazolin-4-one analogs
- Giri, Rajan S.,Thaker, Hardik M.,Giordano, Tony,Williams, Jill,Rogers, Donna,Vasu, Kamala K.,Sudarsanam, Vasudevan
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experimental part
p. 2796 - 2808
(2010/07/06)
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- Solvent-free synthesis of 2-amino-3-aryl-5-substituted thiophenes as anti-inflammatory agents using KF-Al2O3 under microwave irradiation
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The synthesis of 2-amino-3-aryl-5-substituted thiophenes as anti-inflammatory agents catalyzed by KF-Al2O3 under microwave irradiation is reported. Copyright Taylor & Francis Group, LLC.
- Saeidian, Hamdollah,Sadeghi, Azam,Mirjafary, Zohreh,Moghaddam, Firouz Matloubi
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p. 2043 - 2053
(2008/09/21)
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- THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS
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Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
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Page/Page column 14
(2008/06/13)
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- Willgerodt-kindler's microwave-enhanced synthesis of thioamide derivatives
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The Willgerodt-Kindler reaction was applied to a series of aromatic aldehydes and ketones. The reactions were performed in a dipolar aprotic solvent (mainly DMF) in the presence of a base catalyst (4-methylmorpholine) and utilized microwave (mw) irradiation. The pulsed mw technique rather than the continuous irradiation was preferred because it limited side reactions and hydrogen sulfide production. While not always superior to the thermal activation of the reaction, the procedure involving repetitive short pulses of microwave irradiation was found to be faster and result in consistently cleaner products. The technique can be easily applied in a fast parallel synthesis process.
- Poupaert, Jacques H.,Duarte, Sandro,Colacino, Evelina,Depreux, Patrick,McCurdy, Christopher R.,Lambert, Didier L.
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p. 1959 - 1973
(2007/10/03)
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- Design, synthesis, and pharmacological evaluation of some 2-[4-morpholino]-3-aryl-5-substituted thiophenes as novel anti-inflammatory agents: Generation of a novel anti-inflammatory pharmacophore
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We report the synthesis and pharmacological evaluation of some novel 2-morpholino-3-aryl-5-substituted thiophenes, as possible anti-inflammatory leads. The studies culminate in the generation of a novel pharmacophore, which will enable the designing of be
- Pillai, Ajay D.,Rathod, Parendu D.,Xavier, Franklin P.,Vasu, Kamala K.,Padh, Harish,Sudarsanam, Vasudevan
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p. 4667 - 4671
(2007/10/03)
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- Extension of the Willgerodt-Kindler reaction: Protected carbonyl compounds as efficient substrates for this reaction
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Nitrogen derivatives of carbonyl compounds such as oximes, hydrazones, and semicarbazones were found to be excellent candidates for the Willgerodt-Kindler reaction. They can be used directly in a solvent-free reaction, under both classical and microwave conditions, to give the corresponding thiomorpholides in good yields.
- Darabi, Hossein Reza,Aghapoor, Kioumars,Tajbakhsh, Mahmoud
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p. 4167 - 4169
(2007/10/03)
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- A facile synthesis of phenylacetic acids via Willgerodt-Kindler reaction under PTC condition
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Phenylacetic acids are efficiently synthesized from acetophenones via thiomorpholides under Phase Transfer Catalytic (PTC) condition. The reaction proceeds efficiently by using triethyl benzyl ammonium chloride (TEBA) as PTC and the reaction time decreased dramatically upto 1/5th (24-5) to afford pure products in good to excellent yield.
- Alam, Mujahid,Adapa, Srinivas R.
-
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- A versatile one-pot synthesis of 2,3,5-tri-substituted thiophenes from thiomorpholides
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An efficient method for the preparation of 2,3,5-trisubstituted thiophenes in a one-pot synthesis from thiomorpholides via the thio-Claisen rearrangement was developed.
- Matloubi Moghaddam, Firouz,Zali-Boinee, Hassan
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p. 6253 - 6255
(2007/10/03)
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- Synthesis of phenylthioacetomorpholide: Effect of substrate on the Willgerodt-Kindler reaction
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The effect of substrates on the Willgerodt-Kindler reaction was studied. The existence of acidic protons on these substrates accerelates the formation of thiomorpholide was found.
- Darabi, Hossein Reza,Aghapoor, Kioumars,Tabar-Heydar, Kourosh,Nooshabadi, Masoud
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p. 1189 - 1192
(2007/10/03)
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- Reactions of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates
-
2-(Alkoxycarbonylmethylidene)-4-aryl-5-(dialkylamino)thiophen-3(2H)-ones were synthesized by condensation of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates. Intermediate substituted vinylic sulfides were isolated. When heated or in t
- Kosterina, M. F.,Morzherin, Yu. Yu.,Tkachev, A. V.,Rybalova, T. V.,Gatilov, Yu. V.,Bakulev, V. A.
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p. 653 - 658
(2007/10/03)
-
- Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
-
Aldehydes and aryl alkyl ketones were efficiently transformed to thioamides with the same number of carbon atoms via Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions. The thioamides obtained were hydrolyzed to corresponding carboxylic acids with microwave dielectric heating in one minute. Both reactions are very fast and the yields are excellent.
- Matloubi Moghaddam,Ghaffarzadeh
-
p. 317 - 321
(2007/10/03)
-
- A simple route to N,N-dialkyl derivatives of 2-amino-5-thiophenecarboxylates
-
Starting from acetamides 4 and using three different routes - via thioacetamides 5, 3-amino-thioacrylamides 7, or 3-chloropropeniminium salts 6 - a series of new N,N-dialkyl derivatives of 2-amino-5-thiophenecarboxylates 10 has been prepared and analytically and spectroscopically characterized.
- Heyde, Cornelia,Zug, Ines,Hartmann, Horst
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p. 3273 - 3278
(2007/10/03)
-
- Microwave assisted Willgerodt-Kindler reaction of styrenes
-
Styrenes are efficiently transformed to thioamides via the Willgerodt- Kindler reaction under microwave irradiation.
- Moghaddam, Firouz Matloubi,Ghaffarzadeh, Mohammad,Dakamin, Mohammad G.
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p. 228 - 229
(2007/10/03)
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- The rapid synthesis of thiomorpholides by Willgerodt-Kindler reaction under microwave heating
-
The Willgerodt-Kindler reaction of several aryl alkyl ketones with sulfur and morpholine under solvent-free conditions was performed in a domestic microwave oven. Good yields were attained within a very short reaction time (between 3.5-6 min.).
- Nooshabadi, Masoud,Aghapoor, Kioumars,Darabi, Hossein Reza,Mojtahedi, Mohammad Majid
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p. 7549 - 7552
(2007/10/03)
-
- Reactions of N-thioacetylmorpholine anion with iodoarenes and 1-iodoadamantane by the S(RN)1 mechanism
-
The anion of N-acetylthiomorpholine 2 was studied in photostimulated reactions with iodobenzene 1a and 1-iodonaphthalene 1b in DMSO, giving good yields of the substitution products 3a and 3b by the S(RN)1 mechanism. The reaction of 1a with 2 is also induced with FeBr2. 1-Iodoadamantane 4 did not react with the anion of N-acetylmorpholine, but reacted with 2 to give the substitution product 5 under irradiation. By competition experiments, acetophenone enolate ions are 1.4 times more reactive than 2 toward 1a and 3.3 times toward 4.
- Murguia, Marcelo C.,Rossi, Roberto A.
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p. 1355 - 1358
(2007/10/03)
-
- Non-staining and slightly-staining antiozonants
-
There is disclosed compounds having, within their structural formulae, a trivalent moiety: STR1 which exhibit antiozonant activity when added to rubber compositions at antiozonant effective levels and which exhibit synergistic antiozonant activity when used with conventional antiozonants in rubber compositions. There is also disclosed novel compounds which can be used as antiozonants.
- -
-
-
- Optimum Conditions for the Willgerodt-Kindler Reaction. 3. Amine Variation
-
Optimum conditions for the synthesis of phenylacetic acid thioamids by the joint action of elemental sulfur and amines on acetophenons have been studied with the following amines: Morpholine, pyrrolidine, 4-methylpiperidine, isopropylamine, 2-butylamine,
- Lunstedt, Torbjoern,Carlson, Rolf,Shabana, Rashad
-
p. 157 - 163
(2007/10/02)
-
- Optimum Conditions for the Willgerodt-Kindler Reaction 2: A Multivariate Study of the Influence of Different Solvents on the Optimum Reaction Conditions
-
The optimum conditions for synthesis of phenylacetic acid thiomorpholide by the reaction of acetophenone in the presence of morpholine and elemental sulfur have been studied in 13 solvents: N,N-dimethylformamide, triethylene glycol, N-methylacetamide, eth
- Carlson, Rolf,Lundstedt, Torbjoern,Shabana, Rashad
-
p. 694 - 699
(2007/10/02)
-
- Optimum Conditions for the Willgerodt-Kindler Reaction 1: Reaction of Substituted Acetophenones. Prediction of Optimum Conditions for New Substrates by Multivariate Correlation
-
Optimum conditions for the synthesis of p-substituted phenyl-acetic acid thiomorpholides by the joint action of elemental sulfur and morpholine on p-substituted acetophenones have been studied with the following substrates: p-methoxy-, p-N,N-dimethylamino
- Carlson, Rolf,Lundstedt, Torbjoern,Shabana, Rashad
-
p. 534 - 544
(2007/10/02)
-
- Reactions of S-Alkyl-N,N-disubstituted Thioamide Salts. Part 4. Sulphenamidine Derivatives
-
Readily available 3-(α-dialkylaminoalkylidene)-1-alkylthiotriazenes (1) with C-aryl, benzyl, or isopropyl substituents, on being stirred with copper(I) cyanide or copper powder in dichloromethane or toluene solution at room temperature or below, give sulp
- Stansfield, Frank
-
p. 2933 - 2935
(2007/10/02)
-
- Infrared spectra of several thiopiperidides and thiomorpholides
-
Infrared spectra in the 1700-500 cm-1 region have been studied for several types of thiopiperidides (thiobenzoylpiperidides, thiocinnamoylpiperidides and phenylthioacetpiperidides) and for the corresponding thiomorpholides.Three characteristic thioamide bands were located and assigned.The behaviour of these bands on molecular complexing (with iodine as an electron acceptor) was used to support the assignments.The experimental data were discussed in terms of the theoretical results obtained by an HMO procedure.
- Cornea, Felicia,Cercasov, Cornelia,Ciureanu, Mariana
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p. 775 - 782
(2007/10/02)
-
