- Nickel-Catalyzed Reaction of Benzamides with Bicylic Alkenes: Cleavage of C-H and C-N Bonds
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The nickel-catalyzed reaction of aromatic amides that contain an 8-aminoquinoline as a directing group with bicyclic alkenes, such as norbornene and 1,4-dihydro-1,4-epoxynaphthalene, results in the cleavage of both the C-H bond at the ortho-position of th
- Skhiri, Aymen,Chatani, Naoto
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- A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
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Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
- Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 1955 - 1958
(2021/03/02)
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- C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
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An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
- Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
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p. 1352 - 1357
(2021/02/26)
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- Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
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Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
- Liu, Feng,Wu, Na,Cheng, Xu
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p. 3015 - 3020
(2021/05/05)
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- 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
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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.
- Samanta, Suvendu,Ray, Shounak,Bhaduri, Samanka Narayan,Samanta, Partha Kumar,Biswas, Papu
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supporting information
(2020/08/10)
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- Copper/Silver Cocatalyzed Regioselective C5-H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds
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A copper/silver co-catalyzed cross-dehydrogenative coupling reaction is developed to achieve exclusively remote C5-H coupling of 8-aminoquinoline amides with the methylenic sp 3 C-H bond of 1,3-dicarbonyl compounds. This protocol provides a hig
- Zhan, Fuxu,Zhang, Wei,Zhao, Huaiqing
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p. 1007 - 1014
(2020/04/01)
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- Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N -Hydroxyphthalimide Ester
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A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivativ
- Aisha, Aertuke,Jin, Can,Li, Deyu,Sun, Bin,Zhu, Rui,Zhuang, Xiaohui
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p. 677 - 682
(2020/04/08)
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- Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile
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The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr
- Wen, Chunxia,Zhong, Ronglin,Qin, Zengxin,Zhao, Mengfei,Li, Jizhen
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p. 9529 - 9532
(2020/09/03)
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- Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow
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Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.
- Chen, Meng-Yi,Fang, Zheng,Guo, Kai,Lin, Xin-Xin,Liu, Cheng-Kou
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supporting information
p. 6437 - 6443
(2020/11/09)
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- Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C?H Bonds with K18F
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A Cu-mediated ortho-C?H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18F and is compatible with a wide range of functional groups. The reaction is showcased in t
- Lee, So Jeong,Makaravage, Katarina J.,Brooks, Allen F.,Scott, Peter J. H.,Sanford, Melanie S.
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p. 3119 - 3122
(2019/01/25)
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- KOtBu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
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This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.
- Ghosh, Tridev,Jana, Snehasish,Dash, Jyotirmayee
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p. 6690 - 6694
(2019/09/12)
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- Tandem Remote Csp3-H Activation/Csp3-Csp3 Cleavage in Unstrained Aliphatic Chains Assisted by Palladium(II)
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We report here a proof-of-concept for the cleavage of unstrained remote Csp3-Csp3 bonds at room temperature assisted by a directing group, opening up new possibilities to use aliphatic carboxylic acids as suitable alkenyl coupling partners. This strategy involves the Pd-mediated Csp3-H activation directed by a tethered 8-aminoquinoline group, followed by a concerted asynchronous carbene insertion into the Pd-C bond, and an unexpected β-carbon-carbon bond splitting. The insertion of a coupling partner into a Pd-C bond is a novel route to promote C-C bond cleavage, which in contrast to most common methodologies does not rely on the use of strained carbocycles.
- Pérez-Gómez, Marta,Azizollahi, Hamid,Franzoni, Ivan,Larin, Egor M.,Lautens, Mark,García-López, José-Antonio
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p. 973 - 980
(2019/03/04)
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- Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor
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Anxiety and depression are common, highly comorbid psychiatric diseases that account for a large proportion of worldwide medical disability. Glyoxalase 1 (GLO1) has been identified as a possible target for the treatment of anxiety and depression. GLO1 is a Zn2+-dependent enzyme that isomerizes a hemithioacetal, formed from glutathione and methylglyoxal, to a lactic acid thioester. To develop active inhibitors of GLO1, fragment-based drug discovery was used to identify fragments that could serve as core scaffolds for lead development. After screening a focused library of metal-binding pharmacophores, 8-(methylsulfonylamino)quinoline (8-MSQ) was identified as a hit. Through computational modeling and synthetic elaboration, a potent GLO1 inhibitor was developed with a novel sulfonamide core pharmacophore. A lead compound was demonstrated to penetrate the blood-brain barrier, elevate levels of methylglyoxal in the brain, and reduce depression-like behavior in mice. These findings provide the basis for GLO1 inhibitors to treat depression and related psychiatric illnesses.
- Perez, Christian,Barkley-Levenson, Amanda M.,Dick, Benjamin L.,Glatt, Peter F.,Martinez, Yadira,Siegel, Dionicio,Momper, Jeremiah D.,Palmer, Abraham A.,Cohen, Seth M.
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p. 1609 - 1625
(2019/02/14)
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- Iron(III)-catalyzed highly regioselective halogenation of 8-amidoquinolines in water
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A simple protocol of iron(III)-catalyzed halogenation of 8-amidoquinolines in water under mild conditions was developed, affording the 5-halogenlated products in good to excellent yields up to 98%. The reaction mechanism most likely involves a single-elec
- Long, Yang,Pan, Lei,Zhou, Xiangge
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- Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow
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An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhyda
- Shu, Quan,Li, Yaming,Liu, Tong,Zhang, Siyu,Jiang, Linlin,Jin, Kun,Zhang, Rong,Duan, Chunying
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supporting information
p. 3636 - 3642
(2019/05/29)
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- Direct oxytosylation of 8-amidoquinolines by koser's reagent: An efficient strategy for 5-substituted 8-amidoquinolines
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A metal-free remote oxytosylation of 8-amidoquinolines has been achieved using Koser's reagent to produce 5-tosyloxy-8-amidoquinolines in good yields. This method is compatible with various functional groups present on the aromatic ring.
- Begum, Zubeda,Bhavani,Sridhar,Reddy, Basireddy V. Subba
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p. 4089 - 4096
(2018/10/15)
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- C5-Regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides with Selectfluor under metal-free conditions
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A novel and efficient regioselective C-H fluorination of 8-aminoquinoline amides and sulfonamides at the C5 position was achieved. Using Selectfluor as a "F" reagent and HOAc as an additive, the reaction proceeds smoothly via a radical pathway. This metho
- Zhang, Yingchao,Wen, Chunxia,Li, Jizhen
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supporting information
p. 1912 - 1920
(2018/03/23)
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- From Surprising Solvothermal Reaction to Uncommon Zinc(II)-Catalyzed Aromatic C-H Activation Reaction for Direct Nitroquinoline Synthesis
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In this work, we first found a surprising solvothermal reaction for direct dinitration of quinoline derivative. To explore the application in direct nitroquinoline synthesis, this reaction was subsequently modified as an equivalent reaction in a Schlenk tube. More significantly, after a constant attempt, nitrated derivative was obtained in optimized condition with a zinc(II) sulfate catalyst, where some substrates with strong electron-withdrawing group were first nitrated by a directly catalyzed condition. This new zinc(II)-catalyzed aromatic C-H activation reaction is the first example of direct dinitration by a single catalyst, which will be a new facile and environmentally friendly strategy to access synthetically useful nitroquinoline derivative.
- Wang, Yazhen,Yu, Feihu,Han, Xiao,Li, Ming,Tong, Yue,Ding, Jie,Hou, Hongwei
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supporting information
p. 5953 - 5958
(2017/05/22)
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- Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives
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A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.
- Huang, Binbin,Zhao, Yating,Yang, Chao,Gao, Yuan,Xia, Wujiong
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supporting information
p. 3799 - 3802
(2017/07/26)
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- Metal–free C5-H Bromination of Quinolines for One-pot C?X (X=C, O, S) Bond Formations
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We developed an efficient and convenient method for metal-free bromination of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. And this bromination step can be followed in a one-pot manner with five kinds of C?X (X=C, O, S) cross-coupling reactions without any extra workup, such as removal of the solvent or filtration for the separation of intermediate. The reaction tolerates a wide scope of alkyl and aryl amides as well as (hetero)aryl boronic acids, generating the corresponding arylation products in good to excellent yields. Furthermore, the one-pot alkenylation, alkynylation, thiolation and phenoxylation of quinolines on the C5 position can be efficiently realized using this brominated quinoline amide molecular platform. Thus, the method shows high practical potential in industrial organic synthesis. (Figure presented.).
- Li, You,Zhu, Longzhi,Cao, Xin,Au, Chak-Tong,Qiu, Renhua,Yin, Shuang-Feng
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supporting information
p. 2864 - 2873
(2017/08/23)
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- Iron(iii)-catalyzed chelation assisted remote C-H bond oxygenation of 8-amidoquinolines
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Iron catalyzed site selective and chelation assisted C-H functionalization in 8-amidoquinolines is achieved. The remote C5-benzoxylation with benzoyl peroxide produced a variety of potentially bioactive 8-arylcarboxamido-5-benzoyloxy quinoline derivatives. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on carboxamide and acyl peroxide in addition to tolerance of halo-substitutions on either of the aryls. The reaction is additive, silver free and proceeds without the exclusion of air or moisture.
- Vinayak, Botla,Navyasree, Pilli,Chandrasekharam, Malapaka
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p. 9200 - 9208
(2017/11/14)
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- Visible-light-promoted selective C-H amination of heteroarenes with heteroaromatic amines under metal-free conditions
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The regioselective C-H amination of quinoline amides (C5) and imidazopyridines (C3) under transition-metal-free conditions at room temperature with a high degree of functional group tolerance is reported. The C-H amination promoted by visible light in the
- Samanta, Supravat,Ravi, Chitrakar,Rao, Sadu Nageswara,Joshi, Abhisek,Adimurthy, Subbarayappa
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supporting information
p. 9590 - 9594
(2017/11/30)
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- A First Example of Cobalt-Catalyzed Remote C H Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism
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The development of new C H functionalization protocols based on inexpensive cobalt catalysts is currently attracting significant interest. Functionalized 8-aminoquinoline compounds are high-potential building blocks in organic chemistry and pharmaceutical compounds and new facile routes for their preparation would be highly valuable. Recently, copper has been applied as catalyst for the functionalization of 8-aminoquinoline compounds and found to operate through a single electron transfer (SET) mechanism, although requiring elevated reaction temperatures. Herein, we described the first example of a cobalt-catalyzed remote C H functionalization of 8-aminoquinoline compounds operating through a SET mechanism, exemplified using a practical and mild nitration protocol. The reaction uses inexpensive cobalt nitrate hexahydrate [Co(NO3)2?6 H2O] as catalyst and tert-butyl nitrite (TBN) as nitro source. This methodology offers the basis for the facile preparation of many new functionalized 8-aminoquinoline derivatives. (Figure presented.).
- Whiteoak, Christopher J.,Planas, Oriol,Company, Anna,Ribas, Xavi
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supporting information
p. 1679 - 1688
(2016/10/13)
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- Copper(ii)-catalyzed C5 and C7 halogenation of quinolines using sodium halides under mild conditions
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A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording the desired remote C-H activation products in moderate to good yields. This reaction proceeds with low-cost sodium halides (NaX, X =
- Xu, Jun,Zhu, Xiaolei,Zhou, Guobin,Ying, Beibei,Ye, Pingping,Su, Lingying,Shen, Chao,Zhang, Pengfei
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p. 3016 - 3021
(2016/03/19)
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- Transition-metal-free oxidative C5 C-H-halogenation of 8-aminoquinoline amides using sodium halides
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A simple and efficient transition-metal-free oxidative halogenation (Cl, Br) of the C5 C-H bond of 8-aminoquinoline amides has been developed. This method employed low-cost and innoxious sodium halides as halogenation reagents and oxone as an oxidant. The
- Wang, Ying,Wang, Yang,Jiang, Kai,Zhang, Qian,Li, Dong
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supporting information
p. 10180 - 10184
(2016/11/17)
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- Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position
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An efficient and convenient method is developed for the remote C-H bond chalcogenation of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. The protocol makes use of inexpensive CuBr2 as mediator and shows good t
- Zhu, Longzhi,Qiu, Renhua,Cao, Xin,Xiao, Song,Xu, Xinhua,Au, Chak-Tong,Yin, Shuang-Feng
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supporting information
p. 5528 - 5531
(2015/12/01)
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- Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect
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A series of malonamides possessing two quinoline moieties were synthesized and characterized as fluoroionophores for the Zn2+ ion. We focused on the relationship between the substituents introduced to the C2-position of the malonamides and their Zn2+ ion-selectivity, exploiting the structural effect of the substituents in the design of the fluoroionophores with high selectivity. The substituents introduced to the malonamides were the methyl, benzyl and naphthalenylmethyl groups. In dimethyl sulfoxide solvent, all substituted bisquinolinyl malonamides showed excellent fluorescence sensing for the Zn2+ ion, while unsubstituted bisquinolinyl malonamide 1 displayed ratiometric sensing for the Co2+ ion. N,N′-Bis(8-quinolyl)-2-methyl-2-naphthalenylmethyl malonamide 4 exhibited the highest Zn2+ ion-selectivity against the Cd2+ ion. Although the substituents introduced into the C2-position are spatially distant from the quinoline recognition moiety, this study indicated that they greatly influenced the ion selectivities of the bisquinolinyl malonamides. Furthermore, it was demonstrated that visible fluorescence analyses could be performed on malonamide 4.
- Moriuchi-Kawakami, Takayo,Kawata, Keita,Nakamura, Sho,Koyama, Yoshiaki,Shibutani, Yasuhiko
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p. 9805 - 9813
(2015/01/09)
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- Development of new cathepsin b inhibitors: Combining bioisosteric replacements and structure-based design to explore the structure-activity relationships of nitroxoline derivatives
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Human cathepsin B has many house-keeping functions, such as protein turnover in lysosomes. However, dysregulation of its activity is associated with numerous diseases, including cancers. We present here the structure-based design and synthesis of new cathepsin B inhibitors using the cocrystal structure of 5-nitro-8-hydroxyquinoline in the cathepsin B active site. A focused library of over 50 compounds was prepared by modifying positions 5, 7, and 8 of the parent compound nitroxoline. The kinetic parameters and modes of inhibition were characterized, and the selectivities of the most promising inhibitors were determined. The best performing inhibitor 17 was effective in cell-based in vitro models of tumor invasion, where it significantly abrogated invasion of MCF-10A neoT cells. These data show that we have successfully explored the structure-activity relationships of nitroxoline derivatives to provide new inhibitors that could eventually lead to compounds with clinical usefulness against the deleterious effects of cathepsin B in cancer progression.
- Sosi?, Izidor,Mirkovi?, Bojana,Arenz, Katharina,?tefane, Bogdan,Kos, Janko,Gobec, Stanislav
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p. 521 - 533
(2013/04/24)
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- N-Tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl biaryl carboxamides as antagonists of TRPV1
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Starting from the high throughput screening hit (3), novel N-tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl carboxamides have been identified as potent antagonists of the ion channel TRPV1. The N-quinolinylnicotinamide (46) showed excellent potenc
- Westaway, Susan M.,Chung, Ying-Kit,Davis, John B.,Holland, Vicky,Jerman, Jeffrey C.,Medhurst, Stephen J.,Rami, Harshad K.,Stemp, Geoffrey,Stevens, Alexander J.,Thompson, Mervyn,Winborn, Kim Y.,Wright, James
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p. 4533 - 4536
(2007/10/03)
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- Ring-substituted quinolines as potential anti-tuberculosis agents
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We report in vitro antimycobacterial properties of ring-substituted quinolines (series 1-4) constituting 56 analogues against drug-sensitive and drug-resistant M. tuberculosis H37Rv strains. The most effective compounds 2h (R1=R2= c-C6H11, R 3=NO2, series 1) and 13g (R1=OC 7H15, R2=NO2, series 4) have exhibited an MIC value of 1μg/mL against drug-sensitive M. tuberculosis H37Rv strain that is comparable to first line anti-tuberculosis drug, isoniazid. Selected analogues (2d, 2g, 2h, 4e, 6b, 13b, 13g, and 14e, MIC: ≤6.25μg/mL) upon further evaluation against single-drug-resistant (SDR) strains of M. tuberculosis H37Rv have produced potent efficacy in the range between 6.25 and 50μg/mL.
- Vangapandu, Suryanarayana,Jain, Meenakshi,Jain, Rahul,Kaur, Sukhraj,Singh, Prati Pal
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p. 2501 - 2508
(2007/10/03)
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- Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
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This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.
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- Synthesis and Reactions of Some Dihydro and Tetrahydro-4H-Imidazoquinoline Derivatives
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Reaction of phenyl N-(8-quinolyl)carbamate with sodium borohydride afforded 1,2-dihydro-4H-imidazoquinolin-2-one, 2a.The 5,6-double bond of 2a was functionalized by reaction with nitrosyl chloride to give the nitroolefin 4 and by reaction with h
- Saari, Walfred S.,Halczenko, Wasyl,Freedman, Mark B.,Arison, Byron H.
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p. 837 - 840
(2007/10/02)
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