scholarly journals Use of Triphenylphosphine-Bromotrichloromethane (PPh3-BrCCl3) in the Preparation of Acylhydrazines, N-Methylamides, Anilides and N-Arylmaleimides From Carboxylic Acids

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 4
Author(s):  
Abdullah Al-Hemyari ◽  
Areej Hashim ◽  
Muna Bufaroosha ◽  
Thies Thiemann

In certain countries, many of the reagents used to transform carboxylic acids to acyl halides such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphoryl chloride, thionyl chloride and sulfuryl chloride are difficult to come by. Against this background, the authors developed the reaction system triphenylphosphine (PPh3)–bromotrichloromethane (BrCCl3) to prepare acyl halides in situ. In the following, the use of this reagent combination is joined with the reaction of the in situ prepared acyl halides with nitrogen nucleophiles, specifically with hydrazines, methylamine and anilines. The reaction is also used in an intramolecular variant by the reaction of maleanilic acids to N-arylmaleimides.

2015 ◽  
Vol 70 (1) ◽  
pp. 9-27
Author(s):  
Willi Kantlehner ◽  
Ralf Kreß ◽  
Jochen Mezger ◽  
Georg Ziegler

AbstractN,N,N′,N′,N″,N″-Hexamethylguanidinium chloride9cwas prepared by treating the reaction mixture formed fromN,N,N′,N′-tetramethylurea (1a) and phthaloyl chloride (16) with dimethyltrimethylsilylamine15.N,N,N′,N′-Tetramethyl-chloroformamidinium chloride (2a) is an intermediate in this synthesis. The chloroformamidinium chloride2acan also be prepared by treating the urea1awith thionyl chloride or phosphorus pentachloride, respectively. The guanidinium salt9ccan be obtained from the crude2athus prepared and the silylamine15. From urea/phosphoryl chloride adducts and primary aromatic amines have been prepared guanidines38, which are converted toN,N′-diaryl-N,N′,N″,N″-tetramethyl-guanidinium iodides39on treatment with methyl iodide. TheN,N′,N″-trimethyl-N,N′,N″-triphenylguanidinium salt44awas prepared from the chloroformamidinium salt43andN-methylaniline. The guanidinium salt9cis the reaction product when the urea1a/POCl3adduct is treated with the silylamine15.


Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 3844
Author(s):  
Lijuan Li ◽  
Bingdong Li ◽  
Liwei Feng ◽  
Xiaoqiu Zhang ◽  
Yuqian Zhang ◽  
...  

In this work, Au-modified F-TiO2 is developed as a simple and efficient photocatalyst for H2O2 production under ultraviolet light. The Au/F-TiO2 photocatalyst avoids the necessity of adding fluoride into the reaction medium for enhancing H2O2 synthesis, as in a pure TiO2 reaction system. The F− modification inhibits the H2O2 decomposition through the formation of the ≡Ti–F complex. Au is an active cocatalyst for photocatalytic H2O2 production. We compared the activity of TiO2 with F− modification and without F− modification in the presence of Au, and found that the H2O2 production rate over Au/F-TiO2 reaches four times that of Au/TiO2. In situ electron spin resonance studies have shown that H2O2 is produced by stepwise single-electron oxygen reduction on the Au/F-TiO2 photocatalyst.


1990 ◽  
Vol 55 (7) ◽  
pp. 1817-1827 ◽  
Author(s):  
Vojtěch Kmoníček ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Martin Valchář ◽  
...  

2-Nitro, 3-nitro- and 4-nitrobenzoyl chloride were reacted with 1-benzylpiperazine in benzene in the presence of triethylamine and gave the amides IV-VI, the first of which is considered a bioisostere of the antidepressant agent piberaline (I). 2-Dimethylamino-, 3-dimethylamino- and 4-dimethylaminobenzoic acid were treated with thionyl chloride in benzene in the presence of triethylamine or pyridine, and the acid chlorides formed were reacted in situ with 1-benzylpiperazine affording the amides VII-IX. The amides I and IV-VI were transformed by treatment with phosphorus pentasulfide in pyridine to the thioamides X-XIII. 4-(Dimethylaminomethyl)benzoic acid was reacted with 1-benzylpiperazine in dimethylformamide in the presence of N,N'-carbonyldiimidazole and afforded the amide XIV. Heating of ethyl 5-methylimidazole-4-carboxylate with 1-benzylpiperazine to 200-210 °C gave the amide XV together with the unexpected 1-benzyl-4-ethylpiperazine (XVI). The oily or crystalline bases of the amino amides or thioamides were mostly transformed to crystalline salts and characterized by spectra. Out of the compounds prepared only X (V⁄FB-17 070) and XIV (V⁄FB-17 114) showed indications of efficacy in tests which are considered indicative of antidepressant activity. Compounds VII, VIII, and X appeared to be mildly antidopaminergic - similarly like piberaline (I), and compounds IV, V, XI, XIV, and XV on the contrary showed signs of dopaminominetic activity.


Author(s):  
Mohd Azril Riduan ◽  
Mohd Jumain Jalil ◽  
Intan Suhada Azmi ◽  
Afifudin Habulat ◽  
Danial Nuruddin Azlan Raofuddin ◽  
...  

Background: Greener epoxidation by using vegetable oil to create an eco-friendly epoxide is being studied because it is a more cost-effective and environmentally friendly commodity that is safer than non-renewable materials. The aim of this research is to come up with low-cost solutions for banana trunk acoustic panels with kinetic modelling of epoxy-based palm oil. Method: In this study, the epoxidation of palm oleic acid was carried out by in situ performic acid to produce epoxidized palm oleic acid. Results: Banana trunk acoustic panel was successfully innovated based on the performance when the epoxy was applied. Lastly, a mathematical model was developed by using the numerical integration of the 4th order Runge-Kutta method, and the results showed that there is a good agreement between the simulation and experimental data, which validates the kinetic model. Conclusion: Overall, the peracid mechanism was effective in producing a high yield of epoxy from palm oleic acid that is useful for the improvement of acoustic panels based on the banana trunk.


Author(s):  
Okada Masaki ◽  
Katsuhiko Takeuchi ◽  
Kazuhiro Matsumoto ◽  
Tomoharu Oku ◽  
Jun-Chul Choi

Hydroxycarbonylation of alkenes using formic acid (HCOOH) is ideal for the synthesis of various carboxylic acids as a means to develop a sustainable reaction system with lower environmental impact. In...


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