- Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1: H)-ones and coumarins with unactivated alkyl iodides
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We report, for the first time, a visible-light-promoted direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins using readily accessible unactivated alkyl iodides as alkylation reagents. By applying this new approach, a broad range of valuable 3-alkylated quinoxalin-2(1H)-ones and coumarins (55 examples) can be facilely obtained at room temperature, thus showing the wide utility of this protocol. Notably, this practical reaction occurs under metal- and external photocatalyst-free conditions and exhibits a broad substrate scope and high functional-group tolerance.
- Sun, Jun,Yang, Hua,Zhang, Bo
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supporting information
p. 858 - 863
(2022/02/02)
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- Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1: H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions
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Aryl radicals were generated for the first time from cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate under ambient conditions and visible-light illumination in the absence of any additive, metal catalyst, or external photosensitizer. The present arylation of quinoxalin-2(1H)-ones was chemo- and regioselective, and provided good access to various 3-arylquinoxalin-2(1H)-ones. This journal is
- Xie, Long-Yong,Peng, Sha,Yang, Li-Hua,Peng, Cun,Lin, Ying-Wu,Yu, Xianyong,Cao, Zhong,Peng, Yu-Yu,He, Wei-Min
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supporting information
p. 374 - 378
(2021/01/28)
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- 3-aryl-2(1H)-quinoxalinone and synthesis method thereof
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The invention discloses 3-aryl-2(1H)-quinoxalinone and a synthesis method thereof. According to the synthesis method, 2(1H)-quinoxalinone and aryl acyl peroxide are used as raw materials, acetone is used as a solvent at normal temperature, an LED lamp is used as a light source, and 3-aryl-2(1H)-quinoxalinone is synthesized under the irradiation of the LED lamp. The method avoids using any metal, photocatalyst or additive, and has the advantages of mild reaction conditions, simple experimental operation, good reaction selectivity, high product yield, easy product separation and the like.
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Paragraph 0019-0021; 0040-0043; 0050-0059
(2021/02/06)
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- Direct C-H arylation of quinoxalinones with aryl acylperoxides under catalyst-free condition
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A simple and novel method for the direct C-H arylation of quinoxalinones with aryl acylperoxides has been developed. This reaction proceeded smoothly through a radical process under catalyst-free condition, giving the target products in moderate good yields. Such strategy provides a simple and green alternative for the synthesis of 3-arylquinoxalinones.
- Chen, Bajin,Wang, Shengpeng,Song, Jinxing,Wang, Xiaojun,Yu, Bencheng,Yang, Xiaobo
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supporting information
(2020/12/07)
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- Visible-light-induced C[sbnd]H arylation of quinoxalin-2(1H)-ones in H2O
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An efficient visible-light-induced C[sbnd]H arylation of quinoxalin-2(1H)-ones in H2O is developed, which has the advantages of mild reaction conditions, environmental friendliness and good functional group tolerance. This strategy provides a s
- Bao, Hanyang,Lin, Ziyun,Jin, Mengshi,Zhang, Hongdou,Xu, Jun,Chen, Bajin,Li, Wanmei
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supporting information
(2021/02/16)
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- Molecular oxygen-mediated selective hydroxyalkylation and alkylation of quinoxalin-2(1H)-ones with alkylboronic acids
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Herein, an efficient molecular oxygen-mediated method for the selective hydroxyalkylation and alkylation of quinoxalin-2(1H)-ones with alkylboronic acids under transition-metal free conditions has been developed. This strategy demonstrates a broad scope of quinoxalin-2(1H)-ones and alkylboronic acids, giving 3-hydroxyalkylquinoxalin-2(1H)-ones and 3-alkylquinoxalin-2(1H)-ones in moderate-to-good yield. Control experiments reveal that a radical pathway is involved.
- Li, Wanmei,Ni, Zhigang,Ouyang, Yani,Xu, Jun,Yue, Xiaoguang,Zhang, Hongdou,Zhou, Chenxin
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supporting information
(2021/11/22)
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- Direct decarboxylative C[sbnd]H 3-arylation of quinoxalin-2(H)-ones with aryl acyl peroxides leading to 3-arylquinoxalin-2(1H)-ones
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A facile and direct decarboxylative C[sbnd]H 3-arylation of quinoxalin-2(H)-ones with aryl acyl peroxides has been developed for the synthesis of 3-arylquinoxalin-2(1H)-ones under simple heating conditions. The present methodology provides a simple and highly efficient approach to various 3-arylquinoxalin-2(1H)-ones in high yields without the use of any catalyst and additives.
- Bao, Pengli,Lv, Yufen,Wei, Wei,Yue, Huilan
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supporting information
(2020/11/02)
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- Photocatalytic synthesis method of 3-aryl-N-methylquinoxalin-2(1H)-one compound
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The invention discloses a photocatalytic synthesis method of a 3-aryl-N-methylquinoxalin-2(1H)-one compound, wherein the method comprises the steps: carrying out one-pot reaction on an N-methylquinoxalin-2(1H)-one compound and an aryl formyl peroxide comp
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Paragraph 0034-0037; 0042-0050
(2020/12/15)
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- K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- And light-free conditions
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Two facile and effective C-3 arylation protocols of quinoxalin-2(1H)-ones with arylhydrazines and aryl boronic acids respectively via free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. K2
- Dutta, Nibedita Baruah,Bhuyan, Mayurakhi,Baishya, Gakul
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p. 3615 - 3624
(2020/02/06)
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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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- Synthetic method of 3-arylquinoxalin-2(1H)-one derivatives
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The present invention relates to a method for manufacturing quinoxalin-2(1H)-one derivatives in which an aryl group is substituted at position 3 by conducting a reaction of an aryl diazonium salt from quinoxalin-2(1H)-one derivatives by using a visible li
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Paragraph 0030; 0034-0038
(2019/05/11)
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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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- Preparation method of quinoxalinone derivatives
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The invention belongs to the field of organic synthetic chemistry. The invention relates to a preparation method of quinoxalinone derivatives. Specifically, a covalent organic framework material 2D-COF-1 is used as a photocatalyst; and the quinoxaline-2 (
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Paragraph 0025-0028
(2019/12/02)
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- A Catalyst-Free Minisci-Type Reaction: the C–H Alkylation of Quinoxalinones with Sodium Alkylsulfinates and Phenyliodine(III) Dicarboxylates
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A direct C–H alkylation of quinoxalinones at the C-3 position with sodium alkylsulfinates and phenyliodine(III) dicarboxylates has been developed under catalyst-free conditions. A series of 3-alkylquinoxalinones were afforded in moderate to excellent yields in this protocol, which offers a practical and efficient access to biologically interesting 3-alkylquinoxalin-2(1H)-one derivatives.
- Wang, Liping,Zhao, Jiquan,Sun, Yuting,Zhang, Hong-Yu,Zhang, Yuecheng
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p. 6935 - 6944
(2019/11/11)
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- Mild and Direct C-H Arylation of Quinoxalin-2(1 H)-ones with Aryldiazonium Salts under Metal-Free Conditions
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A mild and direct C-H arylation of quinoxazolin-2(1 H)-ones with aryldiazonium salts has been developed. A wide variety of 3-arylquinoxazolin-2(1 H)-ones were synthesized in up to 92% yield at room temperature under metal-free conditions. This strategy tolerates a wide range of functional groups and shows environmental friendliness and practicality.
- Yin, Kun,Zhang, Ronghua
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supporting information
p. 597 - 602
(2017/12/26)
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- Mn(OAc)3*2H2O promoted addition of arylboronic acids to quinoxalin-2-ones
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A simple method has been developed for the synthesis of 3-aryl quinoxalin-2-one derivatives through an oxidative cross-coupling of arylboronic acids with quinoxalin-2-ones using a readily available oxidant Mn(III) acetate dihydrate. This method provides 3-aryl quinoxalin-2-one scaffolds with a broad substrate scope.
- Ramesh, Boora,Reddy, C. Ravikumar,Kumar, G. Ravi,Reddy, B.V. Subba
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supporting information
p. 628 - 631
(2018/01/17)
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- Transition Metal-Free Direct C-3 Arylation of Quinoxalin-2(1H)-ones with Arylamines under Mild Conditions
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A transition metal-free direct C-3 arylation of quinoxalin-2(1H)-ones with arylamines has been explored. This reaction proceeded smoothly through a radical process under mild conditions and produced the desired arylation products in good yields. The reactions proceeded efficiently with a broad range of substrates and functional group tolerance. (Figure presented.).
- Yuan, Jinwei,Liu, Shuainan,Qu, Lingbo
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p. 4197 - 4207
(2017/12/07)
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- Transition Metal-Free Iodosobenzene-Promoted Direct Oxidative 3-Arylation of Quinoxalin-2(H)-ones with Arylhydrazines
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A transition metal-free iodosobenzene-promoted direct oxidative 3-arylation of quinoxalin-2(H)-ones was developed using various arylhydrazines under air. The protocol affords a variety of 3-arylquinoxalin-2(H)-one derivatives in moderate to good yields. This method provides a rapid access to biologically interesting benzo[g]quinoxalinones and pyrido[3,4-b]pyrazinones. The present methodology features high functional group tolerance including base-sensitive groups as well as allyl- and benzyl-substituted quinoxalin-2(H)-ones under mild reaction conditions. (Figure presented.).
- Paul, Sanjay,Ha, Ji Hyeon,Park, Ga Eul,Lee, Yong Rok
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supporting information
p. 1515 - 1521
(2017/05/05)
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- Transition-Metal-Free Direct C-H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts at Room Temperature
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A method of synthesizing 3-arylquinoxalin-2(1H)-ones using diaryliodonium tetrafluoroborates under mild conditions is described. This protocol has a wide substrate scope and enables direct C-H functionalization. The synthetic potential of this coupling was explored using a range of readily accessible diaryliodonium salts and quinoxalin-2(1H)-ones.
- Yin, Kun,Zhang, Ronghua
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supporting information
p. 1530 - 1533
(2017/04/13)
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- Assisted tandem palladium(II)/palladium(0)-catalyzed C-and N-Arylations of quinoxalin-2(1H)-ones in water
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A straightforward assisted tandem palladium(II)-and palladium(0)-catalyzed direct C-3 and N-4 arylation of quinoxalin-2(1H)-ones with boronic acids and aryl halides in water as safe and cheap solvent is reported. This environmentally friendly catalytic protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.
- Carrr, Amandine,Brion, Jean-Daniel,Alami, Mouad,Messaoudi, Samir
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p. 3821 - 3830
(2015/01/16)
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- [Ir(P-OP)]-catalyzed asymmetric hydrogenation of diversely substituted C=N-containing heterocycles
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Iridium(I) complexes of enantiomerically pure phosphine-phosphite ligands ([Ir(Cl)(cod)(P - OP)]) efficiently catalyze the enantioselective hydrogenation of diverse C=N-containing heterocyclic compounds (benzoxazines, benzoxazinones, benzothiazinones, and quinoxalinones; 25 examples, up to 99% ee). A substrate-to-catalyst ratio as high as 2000:1 was reached.
- Nunez-Rico, Jose Luis,Vidal-Ferran, Anton
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supporting information
p. 2066 - 2069
(2013/06/04)
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- Palladium(II)-catalyzed oxidative arylation of quinoxalin-2(1 H)-ones with arylboronic acids
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A straightforward palladium-catalyzed oxidative C-3 arylation of quinoxalin-2(1H)-ones with arylboronic acids is reported. This protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.
- Carrer, Amandine,Brion, Jean-Daniel,Messaoudi, Samir,Alami, Mouad
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p. 5606 - 5609
(2013/11/19)
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- The first general, highly enantioselective lewis base organocatalyzed hydrosilylation of benzoxazinones and quinoxalinones
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The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysis that are readily accessible from (1S,2R)-ephedrine and (1R,2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.
- Xue, Zhou-Yang,Jiang, Yan,Peng, Xiao-Zhi,Yuan, Wei-Cheng,Zhang, Xiao-Mei
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supporting information; experimental part
p. 2132 - 2136
(2010/11/04)
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- Quinoxalin-2-one derivatives, compositions which protect useful plants and comprise these derivatives, and processes for their preparation and their use
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Compounds of the formula (I) and salts thereof in which X is O or S; (Y)n=n substituents Y, n is 0, 1, 2, 3 or 4, R1 is H, OH, NH2, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl or (C1-C10)-alkoxy, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, R2 is H or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, where the radicals Y are as defined in claim 1 are suitable for use as safeners for crop plants or useful plants against the phytotoxic actions of agrochemicals such as pesticides in these plants.
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Page/Page column 37
(2008/06/13)
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- Formal hydride transfer mechanism for photoreduction of 3-phenylquinoxalin-2-ones by amines. Association of 3-phenylquinoxalin-2-one with aliphatic amines
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The photophysical and photochemical behavior of 1-methyl-3-phenylquinoxalin-2-one (MeNQ) and 3-phenylquinoxalin-2-one (HNQ) in the presence of amines is reported. While HNQ fluorescence shows an auxochromic effect and a bathochromic shift with added amine
- De la Fuente,Canete,Zanocco,Saitz,Jullian
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p. 7949 - 7958
(2007/10/03)
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- REARRANGEMENTS OF AROMATIC CARBONYL ARYLHYDRAZONES OF BENZENE, NAPHTHALENE, AND AZULENE
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Aromatic carbonyl arylhydrazones have been shown to undergo two kinds of rearrangement in polyphosphoric acid both involving nitrogen-nitrogen bond cleavage.The first proceeds via insertion of the imine portion in the position ortho to the second nitrogen atom to give o-phenylenediamine intermediates: their evolution depends on the nature of the starting substrate.This reaction has been employed for synthesizing the quinoxalines (5) and the phenanthridines (11), and was demonstrated to be intramolecular.The second reaction path is a sigmatropic rearrangment exclusive to electron-rich aromatic carbonyl hydrazones.
- Benincori, Tiziana,Pagani, Silvia Bradamante,Fusco, Raffaello,Sannicolo, Franco
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p. 2721 - 2728
(2007/10/02)
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