27202-62-6Relevant academic research and scientific papers
Switching from biaryl formation to amidation with convoluted polymeric nickel catalysis
Sen, Abhijit,Dhital, Raghu N.,Sato, Takuma,Ohno, Aya,Yamada, Yoichi M.A.
, p. 14410 - 14418 (2020/12/21)
A stable, reusable, and insoluble poly(4-vinyl-pyridine) nickel catalyst (P4VP-NiCl2) was prepared through the molecular convolution of poly(4-vinylpyridine) (P4VP) and nickel chloride. We proposed a coordination structure of the Ni center in the precatalyst based on elemental analysis and Ni K-edge XANES, and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki?Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to give the corresponding arylamides in up to 99% yield. In contrast, the reaction of aryl halides and amides in the absence of arylboronic acid/ester did not proceed. P4VP-NiCl2 successfully catalyzed the lactamization for preparing phenanthridinone. P4VP-NiCl2 was reused five times without significant loss of catalytic activity. Pharmaceuticals, natural products, and biologically active compounds were synthesized efficiently using P4VPNiCl2 catalysis. Nickel contamination in the prepared pharmaceutical compounds was not detected by ICP-MS analysis. The reaction was scaled to multigrams without any loss of chemical yield. Mechanistic studies for both Suzuki?Miyaura and amidation were performed.
Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes
Peng, Jin-Bao,Li, Da,Geng, Hui-Qing,Wu, Xiao-Feng
supporting information, p. 4878 - 4881 (2019/06/17)
A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes for the synthesis of amides has been developed. A wide range of substrates were well-tolerated and gave the corresponding amides in moderate to good yields. No external oxidant or reductant was needed in this procedure. This procedure provides a redox-economical process for the synthesis of amides.
A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles
Yakuschenko, Igor K.,Pozdeeva, Natal’ya N.,Gadomsky, Svyatoslav Ya.
, p. 834 - 838 (2019/11/14)
[Figure not available: see fulltext.] A novel method for the preparation of 3,4,5-triaryl-substituted 1,2,4-triazoles by the reaction of hydrazides with secondary amides in polyphosphoric ester has been developed. The new method is characterized by mild conditions and ease of synthesis, including the stages of isolation and purification of the product. Additionally, product structures were confirmed by counter synthesis. It was shown that the proposed method is suitable for producing 1,2,4-triazoles with phenolic substituents without the stages of the protection and deprotection of the hydroxyl group. Using the new method, five 3,4,5-substituted 1,2,4-triazoles were obtained for the first time.
Optimization and antifungal activity of amide analogues
Feng, Hui,Leng, Li,Liu, Jia,Tang, Yuanmou,Tang, Pengcheng,Zhang, Chixiang,Tang, Xioarong,Jiao, Shirong
, p. 4029 - 4031 (2013/05/09)
Using salicylic acid as a lead compound, a series of its analogues (compounds 1-16) were designed and synthesized. Their activity of antipathogenic fungi of plants has been evaluated in the laboratory. The results showed that these compounds had certain antifungal activity against Sclerotinia sclerotiorum and Bipolaris maydis (Nisikado et Miyake) Shoem. Among them, the inhibition of growth for 2-(3- fluorophenylcarbamoyl)phenyl acetate (1) and 2-(3-chlorophenylcarbamoyl)phenyl acetate (2) reached 91.1 %, 92.8 % and 90.1 %, 90.1 % at a concentration of 100 mg L-1, respectively.
