42945-78-8Relevant articles and documents
Base catalysis in the Willgerodt-Kindler reaction
Poupaert, Jacques H.,Bouinidane, Karim,Renard, Marc,Lambert, Didier M.,Isa, Majed
, p. 335 - 340 (2001)
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Sulfated tungstate: A green catalyst for synthesis of thiomorpholides via Willgerodt-Kindler reaction
Salim, Suresh D.,Pathare, Sagar P.,Akamanchi, Krishnacharya G.
experimental part, p. 78 - 81 (2012/06/04)
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
Silica-supported fluoroboric acid (HBF4-SiO2) catalyzed highly productive synthesis of thiomorpholides as activators of l-asparaginase as well as the antioxidant agent
Bandgar, Babasaheb P.,Gawande, Shrikant S.,Warangkar, Suchita C.,Totre, Jalinder V.
experimental part, p. 3618 - 3624 (2010/08/03)
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).
Willgerodt-kindler's microwave-enhanced synthesis of thioamide derivatives
Poupaert, Jacques H.,Duarte, Sandro,Colacino, Evelina,Depreux, Patrick,McCurdy, Christopher R.,Lambert, Didier L.
, p. 1959 - 1973 (2007/10/03)
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.