92636-38-9Relevant academic research and scientific papers
Utilization of caffeine carbon supported cobalt catalyst in the tandem synthesis of pyrroles from nitroarenes and alkenyl diols
Balasubramaniam, Bhuvaneshwari,Dhara, Partha,Gupta, Raju K.,Kundu, Sabuj,Panja, Dibyajyoti,Sau, Anirban
, p. 244 - 254 (2021/09/07)
Employing bio-waste caffeine carbon-supported heterogeneous cobalt catalyst, synthesis of various substituted pyrrole derivatives is reported. In this methodology, pyrroles were synthesized through coupling between nitroarenes and alkenyl diols in a tandem manner. Among all the heterogeneous catalysts Co(OAc)2-CC-800 displayed the highest catalytic activity. Preparative scale synthesis of pyrroles and synthesis of anti-tubercular agent 5-(4-(1H-pyrrol-1-yl)phenyl)-1,3,4-oxadiazole-2-thiol revealed the practical applicability of this protocol. Several kinetic experiments and Hammett studies were conducted to understand the probable mechanism and electronic effects on this transformation.
Lactam derivatives and preparation method and application thereof
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Paragraph 0048-0052; 0076; 0080, (2020/02/10)
The invention relates to lactam derivatives and a preparation method and application thereof. Compared with the prior art, the invention provides lactam compounds with a novel structure. The compoundsand compositions thereof have remarkable activity in inhibition of the proliferation of cancer cells (including, but not limited to, the liver cancer cell line HepG2 and the lung cancer cell line A549), and the activity of multiple compounds is in the same order of magnitude as the activity of the commercial drug adriamycin or superior to the activity of adriamycin. The compounds of the inventioncan be prepared from N-substituted pyrrole compounds through a reaction, and the preparation method is convenient, rapid and efficient.
Nickel-catalyzed decarbonylation of: N -acylated N-heteroarenes
Morioka, Toshifumi,Nakatani, Syun,Sakamoto, Yuki,Kodama, Takuya,Ogoshi, Sensuke,Chatani, Naoto,Tobisu, Mamoru
, p. 6666 - 6671 (2019/07/17)
Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.
Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts
Chen, Huangguan,Han, Jianwei,Wang, Limin
supporting information, p. 354 - 363 (2018/02/19)
With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35-96%). Furthermore, with a catalytic amount of TsOH·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.
Copper(I) Oxide/N,N′-Bis[(2-furyl)methyl]oxalamide-Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading
Pawar, Govind Goroba,Wu, Haibo,De, Subhadip,Ma, Dawei
supporting information, p. 1631 - 1636 (2017/05/22)
An easily prepared oxalic diamide is a powerful ligand for the copper-catalyzed coupling of aryl halides with nitrogen heterocycles. Only 1–2 mol% each of copper(I) oxide and N,N′-bis[(2-furyl)methyl]oxalamide (BFMO) are needed to form N-arylation products under mild conditions. More than 10 different types of nitrogen heterocycles are compatible with these conditions, thereby giving the corresponding N-arylation products. (Figure presented.).
Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium-zinc base and regioselectivity-computed CH acidity relationship
Messaoud, Mohamed Yacine Ameur,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Derdour, A?cha,Chevallier, Floris,Halauko, Yury S.,Ivashkevich, Oleg A.,Matulis, Vadim E.,Picot, Laurent,Thiéry, Valérie,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence
supporting information, p. 1475 - 1485 (2016/04/19)
The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl2·TMEDA (1/3 equiv). With N-phenylpyrrole and -indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or ortho to the heteroatom-containing substituent (OMe, Br). The CH acidities of the substrates were determined in THF solution using the DFT B3LYP method in order to rationalize the experimental results.
L-(+)-Tartaric acid and choline chloride based deep eutectic solvent: An efficient and reusable medium for synthesis of N-substituted pyrroles via Clauson-Kaas reaction
Wang, Ping,Ma, Fei-Ping,Zhang, Zhan-Hui
, p. 259 - 262 (2014/11/07)
l-(+)-Tartaric acid-choline chloride based deep eutectic solvent has been found to be an effective promoted medium for Clauson-Kaas reaction of aromatic amines and 2,5-dimethoxytetrahydrofuran. Structurally diverse N-substituted pyrroles were obtained in high to excellent yields under mild conditions. The deep eutectic solvent is inexpensive, non-toxic, reusable and biodegradable.
Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system
Chen, Mao,Buchwald, Stephen L.
supporting information, p. 11628 - 11631 (2013/11/06)
Going to the source: The trifluoromethylation of aryl/heteroaryl iodides has been demonstrated using a flow system, thus enabling a rapid rate of reaction. A broad spectrum of trifluoromethylated compounds was prepared in good to excellent yields using CF3CO2K as the trifluoromethyl source. The process has the advantage of short reaction times and uses convenient [CF3] sources. Copyright
A recyclable magnetic nanoparticles supported antimony catalyst for the synthesis of N-substituted pyrroles in water
Ma, Fei-Ping,Li, Pei-He,Li, Bao-Le,Mo, Li-Ping,Liu, Ning,Kang, Hui-Jun,Liu, Ya-Nan,Zhang, Zhan-Hui
, p. 34 - 41 (2013/06/26)
A new magnetic nanoparticle-supported antimony catalyst was prepared and evaluated as a recoverable catalyst for Clauson-Kaas reaction. The reaction proceeds efficiently in aqueous medium to give the corresponding N-substituted pyrroles in high yield. The immobilized catalyst could be easily recovered by magnetic separation and recycled for six times without significant loss of its catalytic activity.
Novel approach for the synthesis of N-Substituted pyrroles starting directly from nitro compounds in water
Das, Biswanath,Shinde, Digambar Balaji,Kanth, Boddu Shashi,Kumar, Jayprakash Narayan
, p. 548 - 553 (2011/11/29)
A novel approach for a facile high-yielding synthesis of N-substituted pyrroles has been discovered by the treatment of nitroarenes with 2,5-dimethoxytetrahydrofuran using indium in dilute aqueous HCl at room temperature. Taylor & Francis Group, LLC.
