14547-98-9Relevant academic research and scientific papers
Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
supporting information, p. 5049 - 5055 (2021/07/29)
Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
Visible-Light-Promoted C2 Trifluoromethylation of Quinoline N -Oxides
Gao, Guo-Lin,Liang, Ce,Niu, Yan-Ning,Zhuo, Wang-Tao
supporting information, p. 219 - 226 (2019/12/28)
A photoredox catalytic strategy has been described for the direct C2 trifluoromethylation of quinoline N -oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2 tri
2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds
Muta, Ryuhei,Torigoe, Takeru,Kuninobu, Yoichiro
supporting information, (2019/06/13)
The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.
Nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent
Gao, Xianying,Geng, Yang,Han, Shuaijun,Liang, Apeng,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 1551 - 1554 (2018/03/23)
The first nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent has been achieved. Trifluoromethylation proceeds smoothly under mild conditions with moderate functional group compatibility. Notable advantages of this method include the using of low cost of nickel catalyst, and its simple convenient operation.
Revealing the Macromolecular Targets of Fragment-Like Natural Products
Rodrigues, Tiago,Reker, Daniel,Kunze, Jens,Schneider, Petra,Schneider, Gisbert
, p. 10516 - 10520 (2015/09/02)
Fragment-like natural products were identified as ligand-efficient chemical matter for hit-to-lead development and chemical-probe discovery. Relying on a computational method using a topological pharmacophore descriptor and a drug database, several macromolecular targets from distinct protein families were expeditiously retrieved for structurally unrelated chemotypes. The selected fragments feature structural dissimilarity to the reference compounds and suitable target affinity, and they offer opportunities for chemical optimization. Experimental confirmation of hitherto unknown macromolecular targets for the selected molecules corroborate the usefulness of the computational approach and suggests broad applicability to chemical biology and molecular medicine. Target acquired: Hitherto unknown macromolecular targets of the fragment-like natural products goitrin, isomacroin, and graveolinine were discovered through the use of a computational target-prediction tool tailored for natural products. The results suggest that such methods will find application in target discovery for natural products and could inspire the design of new chemical entities for chemical biology and molecular medicine.
Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N -Heterocycles from n -oxides
Larionov, Oleg V.,Stephens, David,Mfuh, Adelphe,Chavez, Gabriel
, p. 864 - 867 (2014/03/21)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles
Larionov, Oleg V.,Stephens, David,Mfuh, Adelphe M.,Arman, Hadi D.,Naumova, Anastasia S.,Chavez, Gabriel,Skenderi, Behije
, p. 3026 - 3036 (2014/05/06)
A Mo/P catalytic system for an efficient gram-scale oxidation of a variety of nitrogen heterocycles to N-oxides with hydrogen peroxide as terminal oxidant has been investigated. Combined spectroscopic and crystallographic studies point to the tetranuclear Mo4P peroxo complex as one of the active catalytic species present in the solution. Based on this finding an optimized catalytic system has been developed. The utility and chemoselectivity of the catalytic system has been demonstrated by the synthesis of over 20 heterocyclic N-oxides.
Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions
Zhu, Chongwei,Yi, Meiling,Wei, Donghui,Chen, Xuan,Wu, Yangjie,Cui, Xiuling
supporting information, p. 1840 - 1843 (2014/05/06)
A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.
Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases
Inamoto, Kiyofumi,Araki, Yuta,Kikkawa, Shoko,Yonemoto, Misato,Tanaka, Yoshiyuki,Kondo, Yoshinori
supporting information, p. 4438 - 4441 (2013/08/23)
Organocatalytic functionalization of heteroaromatic N-oxides was investigated using in situ generated onium amide bases, and C-nucleophiles were efficiently introduced by the sequential addition-elimination reaction under metal-free conditions, affording 2-substituted nitrogen heteroaromatics generally in good to high yields. The Royal Society of Chemistry 2013.
Regioselective bromination of fused heterocyclic N-oxides
Wengryniuk, Sarah E.,Weickgenannt, Andreas,Reiher, Christopher,Strotman, Neil A.,Chen, Ke,Eastgate, Martin D.,Baran, Phil S.
supporting information, p. 792 - 795 (2013/04/10)
A mild method for the regioselective C2-bromination of fused azine N-oxides is presented, employing tosic anhydride as the activator and tetra-n-butylammonium bromide as the nucleophilic bromide source. The C2-brominated compounds are produced in moderate to excellent yields and with excellent regioselectivity in most cases. The potential extension of this method to other halogens, effecting C2-chlorination with Ts2O/TBACl is also presented. Finally, this method could be incorporated into a viable one-pot oxidation/bromination process, using methyltrioxorhenium/urea hydropgen peroxide as the oxidant.
