607-35-2Relevant academic research and scientific papers
Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen
Ksi??ek, Maria,Kubí?ek, Vladimír,Kusz, Joachim,Ma?ecki, Jan Grzegorz,Nycz, Jacek E.,Swoboda, Daniel,Wantulok, Jakub
, (2021/05/29)
The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.
Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage
Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin
supporting information, p. 2559 - 2564 (2021/04/13)
An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.
Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines
Chen, Shanping,Deng, Guo-Jun,Jiang, Pingyu,Ni, Penghui,Tuo, Xiaolong,Wang, Xiaodong
, p. 8348 - 8351 (2020/03/11)
An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.
Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway
Sen, Chiranjit,Sahoo, Tapan,Singh, Harshvardhan,Suresh, Eringathodi,Ghosh, Subhash Chandra
, p. 9869 - 9896 (2019/08/20)
An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.
Synthetic method of 8-nitroquinoline
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Paragraph 0014-0041, (2019/01/17)
The invention provides a synthetic method of 8-nitroquinoline. The synthetic method comprises the following steps: taking ortho-nitroaniline and glycerinum as raw materials, carrying out dehydration in sulfuric acid, and taking iodine-potassium iodide as an oxidizing agent to cyclize 8-nitroquinoline. At the temperature of 60 to 120 DEG C, glycerinum is added dropwise, the dehydration reaction ofglycerinum and sulfuric acid is mild and controllable, and then the cyclization reaction with ortho-nitroaniline is mild and controllable quickly, so that heat release controllability of sharp reaction cannot be caused. An iodine-potassium iodide water solution is used for taking the place of diarsenic pentoxide as an oxidant, the synthetic method is safe and pollution-free, simple in operation and relatively high in yield. The iodine-potassium iodide catalyst is mild, when a back flow becomes clear from muddy, the reaction is basically finished, the phenomenon is obvious, the reaction endpoint is easy to control, gas phase tracking detection can be realized, the post-treatment is simple, little waste water is generated, and the production process is safe and environmentally-friendly.
Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
Pedron, Julien,Boudot, Clotilde,Hutter, Sébastien,Bourgeade-Delmas, Sandra,Stigliani, Jean-Luc,Sournia-Saquet, Alix,Moreau, Alain,Boutet-Robinet, Elisa,Paloque, Lucie,Mothes, Emmanuelle,Laget, Michèle,Vendier, Laure,Pratviel, Geneviève,Wyllie, Susan,Fairlamb, Alan,Azas, Nadine,Courtioux, Bertrand,Valentin, Alexis,Verhaeghe, Pierre
, p. 135 - 152 (2018/06/08)
To study the antiparasitic 8-nitroquinolin-2(1H)-one pharmacophore, a series of 31 derivatives was synthesized in 1–5 steps and evaluated in vitro against both Leishmania infantum and Trypanosoma brucei brucei. In parallel, the reduction potential of all molecules was measured by cyclic voltammetry. Structure-activity relationships first indicated that antileishmanial activity depends on an intramolecular hydrogen bond (described by X-ray diffraction) between the lactam function and the nitro group, which is responsible for an important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from ?1.1 to ?0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above ?0.6 V display activity toward L. infantum. Nevertheless, such relation between redox potentials and in vitro antiparasitic activities was not observed in T. b. brucei. Compound 22 is a new hit compound in the series, displaying both antileishmanial and antitrypanosomal activity along with a low cytotoxicity on the human HepG2 cell line. Compound 22 is selectively bioactivated by the type 1 nitroreductases (NTR1) of L. donovani and T. brucei brucei. Moreover, despite being mutagenic in the Ames test, as most of nitroaromatic derivatives, compound 22 was not genotoxic in the comet assay. Preliminary in vitro pharmacokinetic parameters were finally determined and pointed out a good in vitro microsomal stability (half-life > 40 min) and a 92% binding to human albumin.
High efficiency microwave-assisted synthesis of quinoline from acrolein diethyl acetal and aniline utilizing Ni/Beta catalyst
Li, An,Yang, Zan,Yang, Tao,Luo, Cai-Wu,Chao, Zi-Sheng,Zhou, Cong-Shan
, p. 21 - 25 (2018/07/06)
A facile and solvent-free microwave-assisted approach to quinoline was developed by utilizing both acrolein diethyl acetal and aniline as reagents, firstly employing Ni/Beta zeolite as mild, ecofriendly and low-cost solid catalyst. As high as 83% yield of quinoline was quickly achieved at a short microwave time. The results indicated that the effect of Ni on Beta zeolite not only significantly promoted conversion of acrolein diethyl acetal to effective intermediate but also dramatically accelerated dehydrogenation rate of tetrahydroquinoline/dihydroquinoline to quinoline.
PHENANTHROLINE PHOSPHONIC ACID DERIVATIVE AND PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
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Paragraph 0087-0089, (2017/02/28)
The present invention relates to a novel phenanthroline phosphonic acid compound and a pharmaceutical salt thereof, as well as an application of the compound and the pharmaceutical salt thereof as collagen prolyl hydroxylase inhibitors in the preparation of drugs for preventing or treating collagen prolyl-4-hydroxylase related disease.
4-(8-quinolylazo)resorcinol and 1-(8-quinolylazo)-2-naphthol: Synthesis and sorption properties
Vershinina,Gornukhina,Lubimova,Golubchikov,Semeikin
, p. 2232 - 2235 (2016/10/24)
A methodology of the synthesis of 4-(8-quinolylazo)resorcinol (QAR) and 1-(8-quinolylazo)-2-naphthol (QAN) was developed. The synthesized compounds were used to modify an oxidized charcoal sorbent. The sorbent efficiently adsorbs copper(II) and zinc(II) cations to form surface electroneutral chelate complexes. The conditions of sorption and desorption of zinc(II) and copper(II) were studied.
A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids
Chatterjee, Nachiketa,Bhatt, Divya,Goswami, Avijit
supporting information, p. 4828 - 4832 (2015/05/05)
A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.
