10041-02-8Relevant articles and documents
2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers
Magano, Javier,Chen, Michael H.,Clark, Jerry D.,Nussbaumer, Thomas
, p. 7103 - 7105 (2006)
A new reagent for the deprotection of aromatic methyl ethers, 2-(diethylamino)ethanethiol, is reported. This compound, commercially available as its HCl salt, affords the corresponding phenols in good to excellent yields on a wide variety of substrates. A clear advantage of this method over the use of more common thiols, such as ethanethiol, is the easy extraction of both the deprotecting reagent and the byproduct 2-(diethylamino)ethyl methyl sulfide into the aqueous phase by quenching with dilute acid, which allows an essentially odorless workup.
Quantitative model of the enhancement of peroxidase-induced luminol luminescence
Easton, Patricia M.,Simmonds, Adrian C.,Rakishev, Askar,Egorov, Alexey M.,Candeias, Luis P.
, p. 6619 - 6624 (1996)
Many phenolic compounds are known to enhance the chemiluminescence associated with the horseradish peroxidase-catalyzed oxidation of luminol, but the mechanism of enhancement is still unproved. Using stopped-flow spectrophotometry, we have found that a series of luminescence enhancers react rapidly with the peroxidase reactive intermediates (compound I and compound II) supporting the hypothesis that the enhancement is due to the acceleration of the enzyme turnover. In addition, pulse radiolysis experiments have shown that the enhancers' phenoxyl radicals oxidize luminol, consistent with a redox mediator role for the enhancers. The latter reaction was found to be reversible, showing that enhancers of low reduction potential, which are efficient in accelerating the enzyme turnover, are also scavengers of luminol radicals and therefore luminescence quenchers. Using these data, a simple model is proposed which correctly predicts that the efficiency of a phenolic compound as luminescence enhancer depends on the reduction potential of the respective phenoxyl radical according to a bell-shaped function with a maximum at ~0.8 V.
Preparation method 4 - (imidazol -1 -yl) phenol
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Paragraph 0035; 0037-0040; 0042-0043; 0045-0046; 0048-0050, (2021/10/20)
The invention discloses a preparation method of 4 - (imidazol -1 -yl) phenol, and belongs to the field of in-vitro diagnosis. The catalyst is prepared by taking bromoanisole and imidazole as raw materials. The organic phase is extracted with saturated bri
Practical and Efficient Synthesis of 2-Thio-imidazole Derivative - ZY12201: A Potent TGR5 Agonist
Agarwal, Sameer,Chaubey, Vipin,Chauhan, Rakesh,Jain, Sarika,Joshi, Vivek M.,Mande, Hemant,Pamidimukkala, Padmaja Sudhakar,Pandey, Bipin,Sasane, Santosh,Shah, Kalpesh,Shah, Shailesh R.,Shukla, Mrigendra,Singh, Kumar K.,Sojitra, Chandrakant,Soman, Shubhangi
, p. 1508 - 1514 (2020/11/23)
Early scalable process development for the synthesis of ZY12201, a novel TGR5 receptor agonist, as a potential clinical candidate is described. A practical, efficient, and scalable synthetic route provided ZY12201 in seven steps and 32% overall yield. The
Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides
Bellotti, Peter,Glorius, Frank,Heidrich, Bastian,Huang, Huan-Ming,Pflüger, Philipp M.,Schwarz, J. Luca
supporting information, p. 10173 - 10183 (2020/06/27)
Developing efficient and selective strategies to approach complex architectures containing (multi)stereogenic centers has been a long-standing synthetic challenge in both academia and industry. Catalytic cascade reactions represent a powerful means of rapidly leveraging molecular complexity from simple feedstocks. Unfortunately, carrying out cascade Heck-type reactions involving unactivated (tertiary) alkyl halides remains an unmet challenge owing to unavoidable β-hydride elimination. Herein, we show that a modular, practical, and general palladium-catalyzed, radical three-component coupling can indeed overcome the aforementioned limitations through an interrupted Heck/allylic substitution sequence mediated by visible light. Selective 1,4-difunctionalization of unactivated 1,3-dienes, such as butadiene, has been achieved by employing different commercially available nitrogen-, oxygen-, sulfur-, or carbon-based nucleophiles and unactivated alkyl bromides (>130 examples, mostly >95:5 E/Z, >20:1 rr). Sequential C(sp3)-C(sp3) and C-X (N, O, S) bonds have been constructed efficiently with a broad scope and high functional group tolerance. The flexibility and versatility of the strategy have been illustrated in a gram-scale reaction and streamlined syntheses of complex ether, sulfone, and tertiary amine products, some of which would be difficult to access via currently established methods.
High-performance sono/nano-catalytic system: CTSN/Fe3O4-Cu nanocomposite, a promising heterogeneous catalyst for the synthesis of: N -arylimidazoles
Taheri-Ledari, Reza,Hashemi, Seyed Masoud,Maleki, Ali
, p. 40348 - 40356 (2019/12/25)
Herein, a promising heterogeneous nanoscale catalytic system constructed of chitosan (CTSN, as a polymeric basis), iron oxide nanoparticles (Fe3O4 NPs, as the magnetic agent), and copper oxide nanoparticles (CuO NPs, as the main cata
Functional 1,8-naphthyridine copper(I) complex as efficient catalyst for n-arylation of imidazoles coupling reactions
Gou, Gao-Zhang,Wu, Na,Zhang, Ju-Cheng,Shi, Ling,Liu, Gui-Yang,Liu, Wei,Mang, Chao-Yong,Chi, Shao-Ming
, p. 181 - 185 (2018/02/28)
The functional 1,8-naphthyridine copper(I) complex, synthesized through a non-catalyst C(sp3)-H methylenation, catalyzes the cross-coupling reaction of aryl halides with imidazoles, by C?N bond formation. The Cu(I) complex catalyzes the reaction with a low catalyst loading (1%, molar fraction) and cheap base even under aerobic conditions. The procedure tolerates aryl halides with various functional groups (such as methyl, methoxy, acetyl, fluoro, nitrile and nitro groups) and gives the corresponding coupling products in moderate to high yields.
Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system
Janíková, Kate?ina,Jedinák, Luká?,Volná, Tereza,Canka?, Petr
, p. 606 - 617 (2018/01/01)
A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.
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.).
Cu2O/nano-CuFe2O4: An efficient and magnetically recoverable catalyst for the ligand-free N-arylation of amines and nitrogen heterocycles with aryl halides
Elhampour, Ali,Nemati, Firouzeh,Kaveh, Mahdieh
supporting information, p. 223 - 225 (2016/03/01)
An efficient strategy has been developed for the N-arylation of azoles and aliphatic amines with aryl halide using a Cu2O/nano-CuFe2O4 magnetic composite as the catalyst and KOH as the base. The methodology is found to be applicable to a variety of nitrogen-containing heterocycles, such as imidazole, indole, and pyrrole, as well as aliphatic amines in high yields with practical simplicity under cost-effective "ligand-free" conditions. The magnetic property of the catalyst allowed its fast separation from the reaction medium by an external magnet. Additionally, the inexpensive catalyst could be recycled for five consecutive runs with small drops in catalytic activity.
