5338-44-3Relevant academic research and scientific papers
Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
Chen, Yujie,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
, p. 8226 - 8235 (2021/06/28)
Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.
Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds
Ran, Maogang,He, Jiaxin,Yan, Boyu,Liu, Wenbo,Li, Yi,Fu, Yunfen,Li, Chao-Jun,Yao, Qiuli
supporting information, p. 1970 - 1975 (2021/03/16)
We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.
Utilization of ultrasonic as an approach of green chemistry for synthesis of hydrazones and bishydrazones as potential antimicrobial agents
Younis, Ahmed,Awad, Ghada E. A.
, p. 599 - 610 (2020/05/28)
Hydrazides 3,4, Hydrazones 6a-c, bishydrazones 8a,b, N-hydroxy-N'- arylpropanehydrazonamide 9a,b and 1-(piperidin-1-yl)-N2-arylamidrazones 10a,b were prepared under ultrasonic waves as an approach for green chemistry. a notable good yield and short reaction time were afforded under ultrasonic waves.The structures of compounds were confirmed in terms of spectroscopic and elemental analyses. The invitro antimicrobial activity of the prepared compounds were evaluated. most of compounds exhibited an excellent growth inhibition such as compounds 2, 3 and 8b against gram positive bacteria, while 2, 3, 8b, 9a, 10a and 10b against gram negative bacteria. all of tested compounds have excellent or good antifungal activity except 3.
3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature
Samanta, Suvendu,Ray, Shounak,Bhaduri, Samanka Narayan,Samanta, Partha Kumar,Biswas, Papu
supporting information, (2020/08/10)
A 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed efficient, mild and metal-free method has been developed for direct amide bond synthesis from simple thioacids and amines as starting materials. This methodology is useful for aromatic, aliphatic, and heteroaromatic thioacids as well as primary, secondary, heterocyclic, and even functionalized amines. A wide substrates scope, operationally mild conditions, and acylation of amines without affecting other functional groups such as alcohols, esters, carbodithioates, among others make this strategy very attractive and practical.
Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes
Wippert, Nicolai A.,Jung, Nicole,Br?se, Stefan
supporting information, p. 568 - 572 (2019/09/03)
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates
Guilherme, Fernanda Dias,Simonetti, Julia évelin,Folquitto, Lais Regina Santos,Reis, Adriana Cotta Cardoso,Oliver, Josidel Concei??o,Dias, Amanda Latércia Tranches,Dias, Danielle Ferreira,Carvalho, Diogo Teixeira,Brand?o, Geraldo Célio,Souza, Thiago Belarmino de
, p. 349 - 356 (2019/03/04)
A new series of glycosylated acylhydrazones was synthesized and all the chemical structures were confirmed by High Resolution Mass Spectrometry (HRMS), 1H and 13C Nuclear Magnetic Resonance (1H-NMR; 13C-NMR) and Fourier Transform Infrared (FTIR) spectroscopy methods. The mass accuracy between the calculated and found values observed in HRMS analyses were near or lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. All of the synthesized compounds were screened for their antibacterial, antifungal and antiviral activities. Five compounds (12, 13, 14, 16 and 19) exerted a modest antifungal activity against the strains evaluated. Derivative 14 showed fungicidal activity against Candida glabrata at 173.8 μM and saccharide unit contributed to the increase of the antifungal potential against this strain. New chemical manipulation of derivative 14 can make it possible to obtain new potentially antimicrobial agents.
General rhodium-catalyzed oxidative cross-coupling reactions between anilines: Synthesis of unsymmetrical 2,2′-diaminobiaryls
Shi, Yang,Liu, Jiahui,Yang, Yudong,You, Jingsong
supporting information, p. 5475 - 5478 (2019/05/16)
Described herein is a dual chelation-assisted RhCl3-catalyzed oxidative C-H/C-H cross-coupling reaction of aniline derivatives. The highlight of this methodology is the chemo- and regioselective cross-coupling between electronically similar substrates, which represents a highly challenging task in oxidative Ar-H/Ar-H cross-coupling reactions. Furthermore, this Cp?-free catalytic reaction tolerates a range of functional groups and requires only a low molar ratio of coupling partners. These features expedite the synthesis of unsymmetrical 2,2′-diaminobiaryls.
Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions
Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na
supporting information, p. 2169 - 2172 (2019/11/25)
An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.
Microwave-mediated Green chemistry approach for the synthesis of some chalcone derivatives and evaluation of their anthelmintic activity
Sahoo, Biswa Mohan,Srinivasa Rao,Banik, Bimal Krishna,Sahoo, Kishore Chandra
, p. 1295 - 1299 (2020/06/27)
In the present study, microwave-mediated Green chemistry approach is followed to prepare some chalcone derivatives. For this purpose, microwave heating technology is used as the alternative energy sources to synthesize a series of chalcone derivatives by Claisen-Schmidt condensation of ethyl 4-acetamidobenzoate with various aromatic aldehydes in the presence of ethanolic sodium hydroxide solution followed by dehydration. With the help of microwave, the rate of reaction is increased with less byproduct formation and better yield of the product. The structures of the newly synthesized compounds are confirmed by FT-IR, 1H NMR, mass spectra and CHN analyses. The titled compounds are screened for their anthelmintic activity and significant activity as compared to the standard drug is found. Compounds with electron withdrawing groups are found to be highly potent among the series.
Visible light driven amide synthesis in water at room temperature from Thioacid and amine using CdS nanoparticles as heterogeneous Photocatalyst
Das, Sudipto,Ray, Shounak,Ghosh, Abhisek Brata,Samanta, Partha Kumar,Samanta, Suvendu,Adhikary, Bibhutosh,Biswas, Papu
, (2017/12/28)
Highly efficient photocatalytic thioacid mediated amide synthesis at room temperature using CdS nanoparticles as photocatalyst was observed under a household 30?W CFL in water. The operationally mild reaction was tolerant to a number of functional group substitutions on amine and could be scaled up to gram. This heterogeneous photocatalyst was extremely stable and could easily be recovered by simple centrifugation for at least six recycling reactions without any significant loss of catalytic performance. The possible reaction mechanism for the photocatalytic thioacid mediated amide synthesis over the CdS semiconductor has also been proposed on the basis of experimental observations.
