- 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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- 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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- The rapid synthesis of thiomorpholides by Willgerodt-Kindler reaction under microwave heating
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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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- Reactions of N,N-(dialkyl)arylthioacetamides with dialkyl acetylenedicarboxylates
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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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- 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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- Base-Controlled Three Component Reactions of Amines, Elemental Sulfur, and Styrenes: Synthesis of Thioamides under Metal-Free Conditions
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Three component reactions of olefins, amines, and sulfur were studied. Thioamidation of styrenes is base-controlled, and 2-phenylethanethioamides and benzothioamides were obtained selectively in the presence of two different bases. This protocol offers a simple and efficient procedure for the synthesis of thioamides.
- Zhang, Pingshun,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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p. 14269 - 14276
(2018/11/25)
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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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- 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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- Selective reduction of carbonyl groups in the presence of low-valent titanium reagents
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The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.
- Lin, Wei,Hu, Ming-Hua,Feng, Xian,Fu, Lei,Cao, Cheng-Pao,Huang, Zhi-Bin,Shi, Da-Qing
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p. 2238 - 2242
(2014/04/17)
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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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- 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 16
(2008/06/13)
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- Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
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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
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p. 317 - 321
(2007/10/03)
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- Microwave assisted Willgerodt-Kindler reaction of styrenes
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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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- Optimum Conditions for the Willgerodt-Kindler Reaction 1: Reaction of Substituted Acetophenones. Prediction of Optimum Conditions for New Substrates by Multivariate Correlation
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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
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p. 534 - 544
(2007/10/02)
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- Infrared spectra of several thiopiperidides and thiomorpholides
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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)
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