2759-54-8Relevant academic research and scientific papers
Thermal behaviors of ionic liquids under microwave irradiation and their application on microwave-assisted catalytic Beckmann rearrangement of ketoximes
Lee, Jae Kyun,Kim, Dok-Chan,Song, Choong Eui,Lee, Sang-Gi
, p. 2301 - 2307 (2003)
Microwave-assisted Beckmann rearrangements of ketoximes in room temperature ionic liquids have been accomplished successfully using only 5 mol% of H2SO4 as a catalyst.
A one pot protocol to convert nitro-arenes into: N-aryl amides
Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
, p. 4040 - 4044 (2020/02/04)
A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes
Li, Dandan,Wang, Yan,Jia, Zhenzhen,Ou, Zhaocheng,Dong, Yongrui,Lv, Cunjie,Fu, Guangbin,Liang, Deqiang
, p. 4797 - 4804 (2019/08/12)
The copper-mediated fluroalkylation/cyclization of N-allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3-fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low-costing fluoroalkylated sources and excellent functional group tolerance.
Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
, p. 3532 - 3538 (2018/08/01)
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
Synthesis method of propanil
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Paragraph 0020; 0024; 0028; 0036; 0038, (2018/11/22)
The invention discloses a synthesis method of propanil. The synthesis method comprises the following steps: firstly performing an acylation reaction on chlorobenzene as a raw material and propionyl chloride to produce p-chloropropiophenone, then performing a condensation reaction on the p-chloropropiophenone and hydroxylamine hydrochloride to produce 1-(4-chlorophenyl)-1-acetoxime, then rearranging the 1-(4-chlorophenyl)-1-acetoxime under an acidic condition, and finally chlorinating to obtain the propanil. By the synthesis method, the reaction selectivity in each step is relatively high, no obvious side reaction occurs and the reaction conversion rate is high, so that the reaction yield is high and the product purity is high; a reaction condition is mild; the raw material cost is low; a requirement on reaction equipment is low; phosphorus-containing wastewater discharge is avoided; extension and tolerance are strong; the conversion success rate from trial production to large-scale production is high, and even if the reaction is interrupted, the trial production can be continued in the later stage; and therefore, the synthesis method is suitable for industrial mass production.
Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature
Mei, Chong,Lu, Wenjun
, p. 4812 - 4823 (2018/04/26)
The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
Carbon Tetrabromide/Triphenylphosphine-Activated Beckmann Rearrangement of Ketoximes for Synthesis of Amides
Gao, Peng,Bai, Zijing
supporting information, p. 1673 - 1677 (2017/10/05)
An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphosphine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tolerance and gave various amides in moderate to good yields.
An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C-C Bond Cleavage
Ou, Yang,Qin, Chong,Song, Song,Jiao, Ning
, p. 2971 - 2975 (2015/09/28)
A novel iron-catalyzed transformation of benzyl azides to give the corresponding amides via C-C bond cleavage under mild reaction conditions is developed. This method provides a new synthetic tool for the construction of amides and the opportunity to accomplish C-C functionalization under mild conditions.
Reductive acylation of nitroarenes to anilides by sodium sulfite in carboxylic acids
Ghaffarzadeh, Mohammad,Akhavan, Pegah
supporting information, p. 1417 - 1419 (2016/09/28)
A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite-carboxylic acid system for the first time has been reported. The sodium sulfite reagent provides the colorless reductant in combination with stoichiometric amounts of carboxylic acid and enables the formation of anilides from nitroarenes without any additives in good to excellent yields with high purities and simple work-up. Furthermore, this protocol provides a novel and complementary access to some industrially important chemicals in kilogram scale under mild conditions.
Ligand-enabled triple C-H activation reactions: One-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides
Deng, Youqian,Gong, Wei,He, Jian,Yu, Jin-Quan
supporting information, p. 6692 - 6695 (2014/07/08)
Diverse 4-aryl-2-quinolinones are prepared from propionamides in one pot by ligand-promoted triple sequential C-H activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new C-C bonds and one C-N bond are formed to rapidly build molecular complexity from propionic acid. Building complexity: Diverse 4-aryl-2-quinolinones such as 1 are prepared from propionamides in one pot by pyridine ligand-promoted triple sequential C-H activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new C-C bonds and one C-N bond are formed to rapidly build molecular complexity from propionic acid.
