- A bis(η5-cyclopentadienyl)cobalt complex of a bis-dithiolene: A chemical analogue of the metal centres of the DMSO reductase family of molybdenum and tungsten enzymes, in particular ferredoxin aldehyde oxidoreductase
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The synthesis is described of a bis-ene-1,2-dithiolate pro-ligand, designed to model the stereochemical situation in the cofactor of the tungsten enzyme ferredoxin aldehyde oxidoreductase from Pyrococcus furiosus. Each masked ene-1,2-dithiolate unit is mounted on a pyrano[2,3-b]tetrahydroquinoxaline tricycle, comparable to the pyrano[2,3-g]tetrahydropteridines found in all molybdoenzymes and tungsten analogues. Hydrolytic release of the bis-ligand was confirmed by its entrapment as a double (η5-C5H 5)Co complex.
- Alphonse, France-Aimée,Karim, Rehana,Cano-Soumillac, Céline,Hebray, Marielle,Collison, David,Garner, C. David,Joule, John A.
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- Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones
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Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.
- Ding, Ling,Liu, Yuxiu,Niu, Kaikai,Wang, Qingmin
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supporting information
(2022/01/24)
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- Copper-Catalyzed Divergent C-H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines
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With control by N1-substituents, the switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones is achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using the combination of a copper catalyst and an oxidant. This new protocol features mild reaction conditions, readily available materials, and a broad substrate scope. Gram-scale and mechanistic studies were also investigated. Furthermore, the desired products exhibited excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells, which were tested by MTT assay.
- Feng, Qiong,He, Meiqin,Huang, Huabin,Ji, Fanghua,Jiang, Guangbin,Li, Xuan,Nie, Hongsheng,Wang, Shoucai,Xiong, Zhicheng,Yang, Guang
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supporting information
p. 1859 - 1864
(2022/03/16)
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- Electro-oxidative C-H alkylation of quinoxalin-2(1: H)-ones with organoboron compounds
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Radical cleavage of C-B bonds to accomplish C-H functionalization is synthetically appealing but practically challenging. We report herein a mild electro-oxidative method for efficient C-H alkylation of quinoxalin-2(1H)-ones by means of radical addition reactions of alkyl boronic acids and esters and alkyl trifluoroborates to afford C-C coupled products. This journal is
- Niu, Kaikai,Hao, Yanke,Song, Lingyun,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 302 - 306
(2021/01/28)
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- Electro-oxidative C-H azolation of quinoxalin-2(1H)-ones
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We have developed a practical, general protocol for direct C-H azolation reactions of quinoxalin-2(1H)-ones by electro-oxidative cross-coupling. These mild reactions proceed under metal-, oxidant-, and reagent-free conditions to provide synthetically useful azolated quinoxalin-2(1H)-ones. Furthermore, the reactions can be carried out with a pencil lead as an electrode and a 3 V battery as a power source, revealing the remarkable flexibility of this protocol.
- Ding, Ling,Hao, Yanke,Liu, Yuxiu,Niu, Kaikai,Song, Hongjian,Wang, Qingmin,Zhou, Pan
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supporting information
p. 3246 - 3249
(2021/05/21)
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- Electrochemical chlorination and bromination of electron-deficient C[sbnd]H bonds in quinones, coumarins, quinoxalines and 1,3-diketones
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The electrochemistry-promoted chlorination and bromination of electron-deficient C[sbnd]H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones.
- Yu, Dan,Ji, Ruixue,Sun, Zhihui,Li, Wenjie,Liu, Zhong-Quan
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supporting information
(2021/11/16)
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- Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions
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Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through a multicomponent reaction under mild conditions is described. Such a transformation was performed under transition-metal-free conditions, affording (E)-oximes in a moderate-to-good yield through recrystallization. Our methodology demonstrates a successful combination of a Mannich-type reaction and radical coupling, providing a green and practical approach for the synthesis of potentially bioactive quinoxalinone-containing molecules.
- Xu, Jun,Yang, Huiyong,He, Lei,Huang, Lin,Shen, Jiabin,Li, Wanmei,Zhang, Pengfei
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supporting information
p. 195 - 201
(2021/01/13)
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- K2S2O8-catalyzed highly regioselective amidoalkylation of diverse N-heteroaromatics in water under visible light irradiation
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A K2S2O8-catalyzed versatile C(sp2)-C(sp3) bond formation with N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)-H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles of "green chemistry". The new K2S2O8 catalytic mechanism was investigated with control experiments.
- Chen, Zhi,Li, Jianjun,Ren, Quanlei,Song, Shengjie,Wang, Chaodong,Xu, Ning,Zhou, Jiadi
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supporting information
p. 5753 - 5758
(2021/08/23)
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- Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones
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A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).
- Aganda, Kim Christopher C.,Hong, Boseok,Lee, Anna
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supporting information
p. 1443 - 1448
(2021/01/26)
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- PIDA-induced oxidative C–N bond coupling of quinoxalinones and azoles
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A metal-free promoted direct oxidative C–N bond coupling of quinoxalinones and azoles for the rapid and effective synthesis of potent pharmaceutical important 3-(azol-1-yl)quinoxalin-2-one has been developed. Employing PIDA as the easily available mediator, the desired coupling products were isolated in moderate to excellent yields with a good substrate scope under operational simplicity and mild reaction conditions. Preliminary mechanistic studies suggested that a radical process is likely to be involved in the reaction.
- Wimonsong, Watchara,Yotphan, Sirilata
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supporting information
(2021/01/25)
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- Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis
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Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure.
- Huang, Lin,Xu, Jun,He, Lei,Liang, Chenfeng,Ouyang, Yani,Yu, Yongping,Li, Wanmei,Zhang, Pengfei
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supporting information
p. 3627 - 3631
(2021/05/03)
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- Direct functionalization of quinoxalin-2(1H)-one with alkanes: C(sp2)-H/C(sp3)-H cross coupling in transition metal-free mode
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Considering the significance of pharmaceutically important heterocycles, efficient and highly versatile protocols for the functionalization of diverse heterocycles with easily accessible feedstock are crucial. Here, we have reported selective alkylation of quinoxalin-2(1H)-one with a broad class of hydrocarbons having different C(sp3)-H bonds with varying bond strengths using di-tert-butyl peroxide (DTBP) as an alkoxyl radical mediator for hydrogen atom transfer (HAT). This dehydrogenative coupling approach utilizes feedstock chemicals such as cycloalkanes, cyclic ethers and alkyl arenes as coupling partners. This protocol exhibits good functional group compatibility and selectivity regarding both heterocycles and unactivated alkanes. Moreover, this methodology allows functionalization of relatively strong C-H bonds of adamantane and exclusive selectivity towards 3° C(sp3)-H bonds is observed. We also illustrate the applicability of this C(sp2)-H/C(sp3)-H cross-coupling for practical access to bioactive pharmaceuticals.
- Dagar, Neha,Raha Roy, Sudipta,Singh, Swati
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p. 5383 - 5394
(2021/06/28)
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- Metal-Free Direct Oxidative C?N Bond Coupling of Quinoxalin-2(1H)-ones with Azoles under Mild Conditions
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Direct C3?H amination of quinoxalin-2(1H)-ones with azoles under mild conditions promoted by PIFA has been achieved in good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds through a radical process. In addition, this method could be applied to gram-scale reaction.
- Cai, Yuepiao,Du, Xinyue,Guo, Jingwen,Xia, Qinqin,Zhang, Lina,Zhang, Liting
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supporting information
p. 2230 - 2238
(2021/07/22)
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- N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes
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Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.
- Liu, Fang,Ye, Zhi-Peng,Hu, Yuan-Zhuo,Gao, Jie,Zheng, Lan,Chen, Kai,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
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p. 11905 - 11914
(2021/08/24)
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- Visible Light-Promoted Radical Relay Cyclization/C-C Bond Formation of N-Allylbromodifluoroacetamides with Quinoxalin-2(1 H)-ones
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A visible light-promoted radical relay of N-allylbromodifluoroacetamide with quinoxalin-2(1H)-ones was developed in which 5-exo-trig cyclization and C-C bond formation were involved. This protocol was performed under mild conditions to facilely offer a variety of hybrid molecules bearing both quinoxalin-2(1H)-one and 3,3-difluoro-γ-lactam motifs. These prepared novel skeletons would expand the accessible chemical space for structurally complex heterocycles with potential biological activities.
- Ye, Zhi-Peng,Liu, Fang,Duan, Xin-Yu,Gao, Jie,Guan, Jian-Ping,Xiao, Jun-An,Xiang, Hao-Yue,Chen, Kai,Yang, Hua
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p. 17173 - 17183
(2021/11/18)
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- Palladium-catalyzed direct Hiyama arylation of quinoxalin-2(1H)-ones with aryl siloxanes in water
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An efficient method for palladium-catalyzed direct Hiyama coupling of various quinoxalin-2(1H)-ones with aryl siloxanes has been developed. The protocol provides a convenient access to a variety of useful C3-arylated 1-methylquinoxalin-2(1H)-one derivatives in reasonable yields by using low cost water as a solvent and oxygen as an oxidant.
- Liu, Xinya,Liu, Zhenwei,Xue, Yingying,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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supporting information
(2020/11/19)
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- Metal-free C3-H acylation of quinoxalin-2(1: H)-ones with α-oxo-carboxylic acids
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Direct C3-H acylation of quinoxalin-2(1H)-ones with α-oxocarboxylic acids under thermo conditions promoted by PIDA has been achieved in a moderate to good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds via a radical pro
- Li, Yu,Ni, Hangcheng,Shi, Xingzi,Zhang, Xiaoning,Zhao, Fei,Zhao, Jingwei
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supporting information
p. 6558 - 6563
(2020/09/04)
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- Electrochemically C-H/S-H Oxidative Cross-Coupling between Quinoxalin-2(1 H)-ones and Thiols for the Synthesis of 3-Thioquinoxalinones
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An electrochemical method for the C(sp2)-H thioetherification of quinoxalin-2(1H)-ones with primary, secondary, and tertiary thiols has been reported. Various quinoxalin-2(1H)-ones underwent this thioetherification smoothly under metal- A nd chemical oxidant-free conditions, affording 3-alkylthiol-substituted quinoxalin-2(1H)-ones in moderate to good yields.
- Zhou, Jiadi,Li, Zhonghui,Sun, Zexu,Ren, Quanlei,Zhang, Qiwei,Li, Hu,Li, Jianjun
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p. 4365 - 4372
(2020/04/10)
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- Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1: H)-ones with N -hydroxyphthalimide esters
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We have developed a protocol for electrochemical decarboxylative C3 alkylation of a wide range of quinoxalin-2(1H)-ones under metal- and additive-free conditions. N-Hydroxyphthalimide esters derived from chain, cyclic, primary, secondary, and tertiary carboxylic acids with a broad scope proved to be suitable substrates. This operationally simple protocol performed in an undivided cell under constant-current conditions is suitable for late-stage functionalization of quinoxalin-2(1H)-ones. The reactions can even be carried out with a 3 V battery as a power source, which demonstrates that organic electrosynthesis can be accomplished without the need for specialized equipment.
- Niu, Kaikai,Song, Lingyun,Hao, Yanke,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 11673 - 11676
(2020/10/20)
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- Construction of C(sp2)?C(sp3) Bond between Quinoxalin-2(1H)-ones and N-Hydroxyphthalimide Esters via Photocatalytic Decarboxylative Coupling
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A novel visible-light-driven decarboxylative coupling of alkyl N-hydroxyphthalimide esters (NHP esters) with quinoxalin-2(1H)-ones has been developed. This C(sp2)?C(sp3) bond-forming transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note, a series of 3-primary alkyl-substituted quinoxalin-2(1H)-ones that were difficult to synthesize by previous methods could be obtained in moderate to excellent yields. Additionally, the mild conditions, easy availability of substrates, wide functional group tolerance and operational simplicity make this protocol practical in the synthesis of 3-alkylated quinoxalin-2(1H)-ones.
- Yan, Zhiyang,Sun, Bin,Zhang, Xun,Zhuang, Xiaohui,Yang, Jin,Su, Weike,Jin, Can
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p. 3344 - 3349
(2019/09/06)
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- Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
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Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).
- Jiang, Yang-ye,Dou, Gui-yuan,Zhang, Luo-sha,Xu, Kun,Little, R. Daniel,Zeng, Cheng-chu
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supporting information
p. 5170 - 5175
(2019/11/13)
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- Nickel-catalyzed electrochemical reductive decarboxylative coupling of: N -hydroxyphthalimide esters with quinoxalinones
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Herein the first example of electrochemically enabled, NiCl2-catalyzed reductive decarboxylative coupling of N-hydroxyphthalimide (NHP) esters with quinoxalinones is reported. A range of primary, secondary, tertiary aliphatic carboxylic acids and amino acid-derived esters were tolerated well. This decarboxylative coupling allows access to structurally diverse 3-alkylated quinoxalinones in up to 91% yields.
- Lian, Fei,Xu, Kun,Meng, Wei,Zhang, Haonan,Tan, Zhoumei,Zeng, Chengchu
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supporting information
p. 14685 - 14688
(2019/12/11)
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- Electrochemically dehydrogenative C-H/P-H cross-coupling: Effective synthesis of phosphonated quinoxalin-2(1: H)-ones and xanthenes
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An efficient electrochemical approach for the C(sp2)-H phosphonation of quinoxalin-2(1H)-ones and C(sp3)-H phosphonation of xanthenes has been developed. The chemistry was performed in an undivided cell under constant current conditions and features a wide range of substrates, up to 99% yield and it is free of transition-metal catalysts- A nd external oxidants, thereby providing a straightforward approach for dehydrogenative C-H/P-H cross-coupling. In addition, control experiments disclose that some of the reactions may involve a radical pathway.
- Li, Ke-Jing,Jiang, Yang-Ye,Xu, Kun,Zeng, Cheng-Chu,Sun, Bao-Guo
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supporting information
p. 4412 - 4421
(2019/08/21)
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- Persulfate-promoted oxidative C-N bond coupling of quinoxalinones and: NH -sulfoximines
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The persulfate-meditated oxidative C-N bond coupling of the C-H bond of quinoxalinones and the N-H bond of NH-sulfoximines is reported. The reaction proceeds smoothly under transition metal-free conditions and provides good to excellent yields of sulfoximidoyl-functionalized quinoxalinone products under mild conditions. The optimized conditions were found to be suitable for a range of sulfoximine and quinoxalinone substrates. This reaction offers a new and convenient strategy to directly install the sulfoximine moiety into the C3 position of quinoxalinone.
- Sumunnee, Ladawan,Pimpasri, Chaleena,Noikham, Medena,Yotphan, Sirilata
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supporting information
p. 2697 - 2704
(2018/04/27)
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- Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions
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A highly efficient iodine-catalyzed oxidative cross-dehydrogenative coupling reaction of quinoxalinones and indoles has been developed. Without the requirement of peroxide and acid, this reaction utilizes a catalytic amount of molecular iodine to facilitate the C-C bond formation under ambient air. This simple and easy-to-handle protocol represents an interesting synthetic alternative with a good scope and functional group compatibility.
- Noikham, Medena,Kittikool, Tanakorn,Yotphan, Sirilata
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supporting information
p. 2337 - 2346
(2018/04/16)
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- Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium
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The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin's rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin's rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.
- Dhameliya, Tejas M.,Chourasiya, Sumit S.,Mishra, Eshan,Jadhavar, Pradeep S.,Bharatam, Prasad V.,Chakraborti, Asit K.
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p. 10077 - 10091
(2018/05/31)
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- Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives
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[Figure not available: see fulltext.] A series of quinoxaline O-nucleosides, 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl-1-yl)quinoxalines and 2-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines, was prepared by the reaction of 3,6,7-trisubstituted quinoxalin-2(1H)-ones with the corresponding protected α-chlorosugars in the presence of NaH. The reaction proceeded chemoselectively to give products of O-substitution with β-configuration at anomeric carbon, as proved by NMR data. The deprotection of the 1-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines was achieved by stirring in ammonia-methanol mixture to afford free O-quinoxaline nucleoside analogs.
- Fathalla, Walid
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- Development of potent and selective small-molecule human Urotensin-II antagonists
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This work describes the development of potent and selective human Urotensin-II receptor antagonists starting from lead compound 1, (3,4-dichlorophenyl)methyl{2-oxo-2-[3-phenyl-2-(1-pyrrolidinylmethyl)-1-piperidinyl]ethyl}amine. Several problems relating to oral bioavailability, cytochrome P450 inhibition, and off-target activity at the kappa opioid receptor and cardiac sodium channel were addressed during lead development. hUT binding affinity relative to compound 1 was improved by more than 40-fold in some analogs, and a structural modification was identified which significantly attenuated both off-target activities.
- McAtee, John J.,Dodson, Jason W.,Dowdell, Sarah E.,Girard, Gerald R.,Goodman, Krista B.,Hilfiker, Mark A.,Sehon, Clark A.,Sha, Deyou,Wang, Gren Z.,Wang, Ning,Viet, Andrew Q.,Zhang, Daohua,Aiyar, Nambi V.,Behm, David J.,Carballo, Luz H.,Evans, Christopher A.,Fries, Harvey E.,Nagilla, Rakesh,Roethke, Theresa J.,Xu, Xiaoping,Yuan, Catherine C.K.,Douglas, Stephen A.,Neeb, Michael J.
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scheme or table
p. 3500 - 3503
(2009/04/16)
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- Kynurenic Acid Derivatives. Structure-Activity Relationships for Excitatory Amino Acid Antagonism and Identification of Potent and Selective Antagonists at the Glycine Site of the N-Methyl-D-aspartate Receptor
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Derivatives of the nonselective excitatory amino acid antagonist kynurenic acid (4-oxo-1,4-dihydroquinoline-2-carboxylic acid, 1) have been synthesized and evaluated for in vitro antagonist activity at the excitatory amino acid receptors sensitive to N-me
- Leeson, Paul D.,Baker, Raymond,Carling, Robert W.,Curtis, Neil R.,Moore, Kevin W.,et al.
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p. 1243 - 1252
(2007/10/02)
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