- The kornblum reaction of α-substituted 3-benzyl-1,2-dihydro-2-oxoquinoxalines. Synthesis and structure of 3-benzoyl-2-oxo-1,2-dihydroquinoxaline
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A method has been developed for the preparation of 3-benzoyl-2-oxo-1,2-dihydroquinoxaline by the reaction of 3-(α-chlorobenzyl)-1,2-dihydroquinoxaline under Kornblum reaction conditions to the corresponding α-azido derivative and then acid fission of the latter. The structure of the target ketone has been confirmed by x-ray analysis.
- Mamedov,Kalinin,Gubaidullin,Litvinov,Levin
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- Metal-free oxidative coupling of quinoxalin-2(1: H)-ones with arylaldehydes leading to 3-acylated quinoxalin-2(1 H)-ones
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A facile TBHP-mediated direct oxidative coupling of quinoxalin-2(1H)-ones with arylaldehydes has been developed under metal-free conditions. This method provided a convenient and efficient approach to various 3-acylated quinoxalin-2(1H)-ones from readily available starting materials with excellent regioselectivity. This reaction proceeded efficiently under mild conditions over a broad range of substrates and with functional group tolerance.
- Yuan, Jin-Wei,Fu, Jun-Hao,Liu, Shuai-Nan,Xiao, Yong-Mei,Mao, Pu,Qu, Ling-Bo
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- Oxidative dehydrobromination of 3-(α-bromobenzyl)quinoxalin-2(1H)- ones according to Kornblum as a simple and efficient synthetic route to quinoxalyl aryl ketones
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Condensation of ethyl 3-aryl-3-bromo-2-oxopropanoates with o-phenylenediamine in acetic acid gave 3-(α-bromobenzyl)quinoxalin-2(1H)- ones which were converted in high yield into the corresponding 3-aroylquinoxalin-2(1H)-ones via oxidative dehydrobrominati
- Gorbunova,Mamedov
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- Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles
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An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.
- He, Xiang-Kui,Li, Lei,Lu, Juan,Xuan, Jun,Ye, Hai-Bing
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supporting information
(2021/11/27)
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- Intramolecular oxidative rearrangement: I2/TBHP/DMSO-mediated metal free facile access to quinoxalinone derivatives
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Iodine/TBHP/DMSO mediated oxidative rearrangement of 3-styrylquinoxalin-2(1H)-one led to the formation of 3-aroylquinoxalin-2(1H)-ones in good to high yields via Kornblum oxidation. This methodology proceeds under mild conditions via oxidative aryl migrat
- Slathia, Nancy,Gupta, Annah,Kapoor, Kamal K.
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- Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones
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Visible light promoted eosin Y catalyzed selective C3-H acylation of quinoxalin-2(1H)-ones has been developed in a green and sustainable manner. In contrast to the conventional anionic eosin Y-based photoredox process, neutral eosin Y acts as the actual c
- Ni, Hangcheng,Li, Yu,Shi, Xingzi,Pang, Yi,Jin, Congying,Zhao, Fei
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supporting information
(2021/03/03)
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- Preparation method 3 -acyl quinoxalinone derivatives
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The invention discloses a method for preparing a 3-acyl quinoxaline ketone derivative (I) and belongs to the field of organic chemistry The method comprises the following steps: by taking a substituted quinoxaline-2-ketone derivative and aldehyde or benzyl alcohol as raw materials, and a 70% tert-butyl hydroperoxide (TBHP) solution as an oxidant, performing a heating reaction in a solvent withoutmetal catalysis, thereby synthesizing the 3-acyl quinoxaline ketone derivative. Compared with a conventional synthesis method, the method has the advantages that firstly, the raw materials are cheap and easy to obtain, the 3-acyl quinoxaline ketone derivative is synthesized at one step, the cost is low, and good application prospects can be achieved; secondly, the method is gentle in reaction condition, high in yield, convenient to operate, beneficial to industrial production and the like, and the reactions are carried out under an air condition. The derivative has potential application in fields such as medicines, chemical engineering and materials, and the invention provides a novel way for synthesis of 3-acyl quinoxaline ketone derivatives. (Refer to Specification).
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Paragraph 0019-0022
(2020/11/22)
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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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- Photoredox Catalyst Free, Visible Light-Promoted C3?H Acylation of Quinoxalin-2(1H)-ones in Water
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A method for the synthesis of 3-acyl quinoxalin-2(1H)-ones through visible-light promoted decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones was developed. The reaction was performed in aqueous phase and photoredox catalyst was not required to run the process. (Figure presented.).
- Lu, Juan,He, Xiang-Kui,Cheng, Xiao,Zhang, Ai-Jun,Xu, Guo-Yong,Xuan, Jun
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supporting information
p. 2178 - 2182
(2020/03/19)
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- Visible-light-induced decarboxylative acylation of quinoxalin-2(1: H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- And external photocatalyst-free conditions
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A mild and eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones and α-oxo carboxylic acids with ambient air as the sole oxidant at room temperature was established. The reaction proceeded efficiently without any metal cata
- Xie, Long-Yong,Bai, You-Shu,Xu, Xiang-Qin,Peng, Xia,Tang, Hai-Shan,Huang, Ying,Lin, Ying-Wu,Cao, Zhong,He, Wei-Min
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supporting information
p. 1720 - 1725
(2020/03/26)
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- Activated carbon/Br?nsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors
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Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under “on-water” condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery.
- Guan, Qi,Cong, Lin,Wang, Qing,Yu, Changyue,Bao, Kai,Zhou, Kai,Wu, Lan,Zhang, Weige
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- Silver-catalyzed decarboxylative acylation of quinoxalin-2(1: H)-ones with α-oxo-carboxylic acids
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A novel silver-catalyzed decarboxylative acylation of α-oxo-carboxylic acids was developed, by which various 3-acyl quinoxalin-2(1H)-ones were synthesized by direct C-H bond acylation of quinoxalin-2(1H)-ones. In this method, α-oxo-carboxylic acids served
- Zeng, Xiaobao,Liu, Chulong,Wang, Xingyong,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
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supporting information
p. 8929 - 8935
(2017/11/09)
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- Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones
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A novel and practical synthesis of 3-benzoylquinoxalin-2(1H)-ones from benzodiazepin-2-ones in two steps from commercially available starting materials is reported. The reaction was achieved in the presence of N-bromosuccinimide in DMSO which served both
- Mtiraoui, Hasan,Renault, Kevin,Sanselme, Morgane,Msaddek, Moncef,Renard, Pierre-Yves,Sabot, Cyrille
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p. 3060 - 3068
(2017/04/10)
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- A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
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A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.
- Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.
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supporting information
p. 1403 - 1416
(2013/02/23)
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- 3-(α-azidoalkyl)quinoxalin-2(1H)-ones and related alkylquinoxalinyl ketones
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A convenient method has been developed for the synthesis of 3-alkanoyl-and 3-benzoyl-2-oxo-1,2-dihydroquinoxalines from the corresponding 3-(α-azidoalkyl)quinoxalines using acetic acid.
- Mamedov,Saifina,Berdnikov
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p. 470 - 473
(2008/12/21)
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- Novel 3-benzoyl-2-piperazinylquinoxaline derivatives as potential antitumor agents
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A series of new benzoylquinoxaline derivatives (7-26) was synthesized and evaluated for antitumor activity against a panel of 60 human cell lines at the NCI of Bethesda. Among the compounds which have passed the preliminary screening, compound 23 exhibite
- Piras, Sandra,Loriga, Mario,Carta, Antonio,Paglietti, Giuseppe,Costi, M. Paola,Ferrari, Stefania
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p. 541 - 548
(2007/10/03)
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- Imidazo[1,5-a]- and thiazolo[3,4-a]-Quinoxalines based on 3-(α-thiocyano-benzyl)quinoxalin-2(1H)-one
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When 3-(α-thiocyanobenzyl-2(1H)-one is heated, competing processes of [a]-annelation of the imidazole or thiazole rings occurs with formation of imidazo[1,5-a]- and thiazolo[3,4-a]quinoxalin-4(5H)-ones.
- Mamedov,Kalinin,Rizvanov,Azancheev,Efremov,Levin
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p. 1121 - 1129
(2007/10/03)
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