- 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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- 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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- 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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- 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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- 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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- 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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p. 653 - 658
(2007/10/03)
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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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- 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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p. 7549 - 7552
(2007/10/03)
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- SOLVENT EFFECT IN THE WILLGERODT-KINDLER REACTION
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The Willgerodt-Kindler reaction was studied on three different model compounds (4-bromobenzaldehyde, 4-fluorobenzaldehyde, 4-methoxyacetophenone) with particular emphasis on the influence of the solvent on the yield of the reaction.Best conditions involved the use of polar aprotic solvents such as DMF.This finding was applied to the Willgerodt-Kindler reaction of two difficult substrates, i.e. 3-methyl-6-formyl-2(3H)-benzoxazolinone and 3-methyl-6-formyl-2(3H)-benzothiazolinone with various secondary amines.
- Kanyonyo, Martial R.,Ucar, Huseyin,Isa, Majed,Carato, Pascal,Lesieur, Daniel,et al.
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- Scope of Organic Synthetic Reactions. Multivariate Methods for Exploring the Reaction Space. An Example with the Willgerodt-Kindler Reaction.
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New principles are presented by which the scope and limitations of synthetic reactions can be determined when substrates, reagents and solvents are allowed to vary sumaltaneously.The strategies are based on multivariate statistical methods: (a) Characteri
- Carlson, Rolf,Lundstedt, Torbjoern
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p. 164 - 173
(2007/10/02)
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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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