cas 59-31-4, 2-Quinolinol | Articles data

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Miller et al.
p. 4763
(1950)
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Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis
The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.
Zhou, Min-Jie,Zhang, Lei,Liu, Guixia,Xu, Chen,Huang, Zheng
supporting information
p. 16470 - 16485
(2021/10/20)

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds
An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.
Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 1611 - 1615
(2021/03/03)

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
supporting information
p. 5049 - 5055
(2021/07/29)

Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
supporting information
p. 5599 - 5604
(2021/08/01)

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information
p. 3071 - 3078
(2021/07/22)

Facile N-Formylation of Amines on Magnetic Fe3O4?CuO Nanocomposites
A facile, eco-friendly, efficient, and recyclable heterogeneous catalyst is synthesized by immobilizing copper impregnated on mesoporous magnetic nanoparticles. The surface chemistry analysis of Fe3O4?CuO nanocomposites (NCs) by XRD and XPS demonstrates the synergistic effect between Fe3O4 and CuO nanoparticles, providing mass-transfer channels for the catalytic reaction. TEM images clearly indicate the impregnation of CuO onto mesoporous Fe3O4. This hydrothermally synthesized eco-friendly and highly efficient Fe3O4?CuO NCs are applied as a magnetically retrievable heterogeneous catalyst for the N-formylation of wide range of aliphatic, aromatic, polyaromatic and heteroaromatic amines using formic acid as a formylating agent at room temperature. The catalytic activity of the NCs for N-formylation is attributable to the synergistic effect between Fe3O4 and CuO nanoparticles. The N-formylated product is further employed for the synthesis of biologically active quinolone moieties.
Datta Khanal, Hari,Mishra, Kanchan,Rok Lee, Yong
p. 4477 - 4484
(2021/08/30)

A photochemical C=C cleavage process: Toward access to backbone N-formyl peptides
Photo-responsive modifications and photo-uncaging concepts are useful for spatiotemporal control of peptides structure and function. While side chain photo-responsive modifications are relatively common, access to photo-responsive modifications of backbone N-H bonds is quite limited. This letter describes a new photocleavage pathway, affording N-formyl amides from vinylogous nitroaryl precursors under physiologically relevant conditions via a formal oxidative C=C cleavage. The N-formyl amide products have unique properties and reactivity, but are difficult or impossible to access by traditional synthetic approaches.
Ball, Zachary T.,Wang, Haopei
supporting information
p. 2932 - 2938
(2022/01/12)

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid
Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.
Song, Zhi-Qiang,Wang, Dong-Hui
supporting information
p. 8470 - 8474
(2020/11/18)

Identification of N-acyl quinolin-2(1H)-ones as new selective agents against clinical isolates of Acanthamoeba keratitis
A collection of N-substituted quinolin-2(1H)-ones were screened against a panel of clinically relevant protozoa (Leishmania, Trypanosoma and Acanthamoeba). Three quinolin-2(1H)-one compounds were identified as selective anti-Acanthamoeba agents. Further assessment revealed that these compounds were active against both trophozoite and cyst forms of A. castellanii Neff, and caused protozoa death via apoptosis. The data presented herein identify N-acyl quinolin-2(1H)-ones as a promising new class of selective anti-Acanthamoeba agents.
Abad-Grillo, Teresa,Lorenzo-Morales, Jacob,McNaughton-Smith, Grant,Freijo, Mónica Blanco,López-Arencibia, Atteneri,Pi?ero, José E.,Reyes-Batlle, María
(2020/04/08)

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
Li, Yushu,Wong, Luet L.
p. 9551 - 9555
(2019/08/06)

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines
We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.
Angeli, Andrea,Trallori, Elena,Carta, Fabrizio,Di Cesare Mannelli, Lorenzo,Ghelardini, Carla,Supuran, Claudiu T.
supporting information
p. 947 - 951
(2018/09/12)

Direct Palladium-Catalyzed β-Arylation of Lactams
A direct and catalytic method is reported here for β-arylation of N-protected lactams with simple aryl iodides. The transformation is enabled by merging soft enolization of lactams, palladium-catalyzed desaturation, Ar?X bond activation, and aryl conjugate addition. The reaction is operated under mild reaction conditions, is scalable, and is chemoselective. Application of this method to concise syntheses of pharmaceutically relevant compounds is demonstrated.
Chen, Ming,Liu, Feipeng,Dong, Guangbin
p. 3815 - 3819
(2018/03/13)

Preparation method of 2-quinolinone compounds
The invention provides a preparation method of 2-quinolinone compounds. Quinoline-N-oxide compounds are served as raw materials and react in an organic solvent in the presence of zinc salt served as acatalyst and under the illumination of an xenon lamp, a series of 2-quinolinone compounds are synthesized. The preparation method provided by the invention has the following beneficial effects: as animportant nitrogen-containing heterocyclic compound, the quinolinone compounds are already applied to the fields such as medicine and important reaction intermediates and have a broad prospect in market application. According to the preparation method provided by the invention, quinoline-N-oxides are served as raw materials and react in the organic solvent in the presence of cheap metal salt served as a catalyst and in the condition of illumination, a series of 2-quinolinone compounds are synthesized; the method has the advantages of simple steps, easily available raw materials, mild reactionconditions, accordance to the principles of green chemistry and the like. The preparation method provided by the invention has relatively great use value and social and economic benefits.
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Paragraph 0029; 0030; 0031

(2018/12/05)

Palladium-catalyzed synthesis of quinolin-2(1: H)-ones: the unexpected reactivity of azodicarboxylate
Quinolin-2(1H)-one is a useful structure unit present in a wide range of natural products and pharmaceuticals. A Pd(ii)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides was developed with azodicarboxylates which act as both the activating agent and oxidant. The reaction proceeded under mild conditions and no protection against air and moisture was needed.
Peng, Jin-Bao,Chen, Bo,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
supporting information
p. 1632 - 1635
(2018/03/21)

2 - (1 H) - quinoline compound of microwave-assisted synthesis method (by machine translation)
The invention belongs to the field of organic intermediate synthesis, in particular discloses a 2 - (1 H) - quinoline compound of microwave-assisted synthetic method: quinoline raw material, and water in a reaction promoter and microwave under the assistance of the addition reaction, to obtain the 2 - (1 H) - quinoline compound; the quinoline raw material is quinoline, or on the quinoline ring in addition to the 2 other than the position of the substituent on the quinoline derivatives containing; the reaction accelerator is 2 - chloroethyl ester and/or 2 - [...] ester. The method raw materials are easy, simple reaction conditions, the reaction time is short, green energy-saving, reaction selectivity and high yield, excellent substrate functional group compatibility, and has high application value. (by machine translation)
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Paragraph 0061-0062; 0094-0099; 0103-0108; 0112-0123

(2018/09/28)

Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions
A practical and environmentally attractive methodology for the direct diversification of N-heterocycles at ambient temperature under open-air conditions was developed. The obvious advantage of the process is that no toxic reagent, transition metal, base or other additive is employed, thus greatly reducing costs, facilitating post-reaction neutralization and purification and minimizing the environmental impact.
Xie, Long-Yong,Qu, Jie,Peng, Sha,Liu, Kai-Jian,Wang, Zheng,Ding, Man-Hua,Wang, Yi,Cao, Zhong,He, Wei-Min
supporting information
p. 760 - 764
(2018/02/14)

The Diverse One-Pot Reactions of 2-Quinolylzincates: Homologation, Electrophilic Trapping, Hydroxylation, and Arylation Reactions
2-Quinolylzincates were efficiently produced from the regioselective metalation reactions of quinoline with various organozincates as key intermediates. The four different types of title reactions of these intermediates under the presented reaction conditions allowed for the facile formation of the corresponding C-2 functionalized quinolines, which are not successfully accessed through typical zincation methods.
Jeong, Hye Jin,Chae, Suyeon,Jeong, Keunhong,Namgoong, Sung Keon
supporting information
p. 6343 - 6349
(2018/10/31)

C-Bridged Bispyrrolidines and Bispiperidines as New Ligands
The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.
Stumpf, Tim-Daniel J.,Steinbach, Manfred,H?ltke, Magdalene,Heuger, Gerold,Grasemann, Franka,Fr?hlich, Roland,Schindler, Siegfried,G?ttlich, Richard
p. 5538 - 5547
(2018/10/25)

Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline
In this study, we designed and synthesized twenty new derivatives of 2-(4-benzoyl-1-piperazinyl)- quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and 13C NMR spectroscopy and MS spectrometry. The activity of novel compounds was evaluated in the cell viability assay as well as in the wound healing assay. Presented data show that examined substances have anticancer activity in cell culture. Seven compounds which showed a high rate of cell growth inhibition were selected for further studies. Three of them strongly reduced the growth of B16F10 cells. The novel compounds constitute a good base for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs.
Kubica, Krzysztof P.,Taciak, Przemys?aw P.,Czajkowska, Agnieszka,Stokfisz-Ignasiak, Alicja,Wyrebiak, Rafa?,Podsadni, Piotr,M?ynarczuk-Bia?y, Izabela,Malejczyk, Jacek,Mazurek, Aleksander P.
p. 891 - 901
(2018/09/25)

Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones
The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.
Chen, Ming,Rago, Alexander J.,Dong, Guangbin
supporting information
p. 16205 - 16209
(2018/11/23)

Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
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.
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)

A nitrogen oxide C2 - bit hydroxylated method (by machine translation)
The present invention relates to nitrogen oxide C2 - bit hydroxylated method, in particular under reflux conditions in dichloroethane, three pyrrole alkyl bromide (PyBrop) [...] phosphate, sodium acetate, water and nitrogen oxides produced by the reaction of hydroxyl-substituted product. The process has simple operation, mild condition, high reaction selectivity, substrate wide applicability, high yield and the like. The application for the first time using this method to synthesize a series of 2 - hydroxyquinoline, 2 - hydroxy pyridine and 1 - hydroxy isoquinoline compound, in the establishment of the compounds of the library synthesis application have broad prospects. (by machine translation)
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0038

(2017/05/19)

Design of a biased potent small molecule inhibitor of the bromodomain and PHD finger-containing (brpf) proteins suitable for cellular and in vivo studies
The BRPF (bromodomain and PHD finger-containing) family are scaffolding proteins important for the recruitment of histone acetyltransferases of the MYST family to chromatin. Evaluation of the BRPF family as a potential drug target is at an early stage although there is an emerging understanding of a role in acute myeloid leukemia (AML). We report the optimization of fragment hit 5b to 13-d as a biased, potent inhibitor of the BRD of the BRPFs with excellent selectivity over nonclass IV BRD proteins. Evaluation of 13-d in a panel of cancer cell lines showed a selective inhibition of proliferation of a subset of AML lines. Pharmacokinetic studies established that 13-d had properties compatible with oral dosing in mouse models of disease (Fpo 49%). We propose that NI-42 (13-d) is a new chemical probe for the BRPFs suitable for cellular and in vivo studies to explore the fundamental biology of these proteins.
Igoe, Niall,Bayle, Elliott D.,Fedorov, Oleg,Tallant, Cynthia,Savitsky, Pavel,Rogers, Catherine,Owen, Dafydd R.,Deb, Gauri,Somervaille, Tim C. P.,Andrews, David M.,Jones, Neil,Cheasty, Anne,Ryder, Hamish,Brennan, Paul E.,Müller, Susanne,Knapp, Stefan,Fish, Paul V.
supporting information
p. 668 - 680
(2017/02/05)

Rhodium(III)-catalyzed and MeOH-involved regioselective mono-alkenylation of: N -arylureas with acrylates
We herein disclose, for the first time, Rh(iii)-catalyzed and MeOH-involved regioselective mono-alkenylation of arenes with acrylates using NHCONMe2 as the transformable directing group, giving direct access to diverse ortho-acrylated N-phenyl
Lv, Honggui,Shi, Jingjing,Huang, Junjun,Zhang, Chao,Yi, Wei
p. 7088 - 7092
(2017/09/07)

Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism
Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.
Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho
p. 13756 - 13767
(2017/12/26)

Cp?Ir-Catalyzed Acceptorless Dehydrogenation of Carbon-Carbon Single Bonds
Pentamethylcyclopentadienyl (Cp?) iridium(III) chloride catalyzed acceptorless dehydrogenation of α-tetralone is reported. Cp? iridium chloride showed higher activity in comparison to other Cp? iridium complexes having bromide, iodide, or hydride or complexes without a Cp ring. The desired product, naphthol, was obtained in up to 71% yield from α-tetralone. The dehydrogenation by Cp? iridium catalyst could be applied to not only α-tetralone but also dihydrocoumarin, dihydroquinolinone, dimethylcyclohexanone, dihydrobenzofuran and 1-isochromanone, although the conversion stayed moderate. The catalytic turnover was not limited by the increased concentration of the product but by catalyst decomposition.
Ando, Hideaki,Kusumoto, Shuhei,Wu, Weiwei,Nozaki, Kyoko
supporting information
p. 2317 - 2322
(2017/06/30)

Iron-catalyzed aerobic oxidative cleavage of the C-C σ-bond using air as the oxidant: Chemoselective synthesis of carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds
A simple iron-catalyzed aerobic oxidative C-C σ-bond cleavage of ketones has been developed. Readily available and environmentally benign air is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, chemoselectively yielding carbon chain-shortened aldehydes, ketones and 1,2-dicarbonyl compounds without overoxidation.
Xing, Qi,Lv, Hui,Xia, Chungu,Li, Fuwei
p. 489 - 492
(2016/01/12)

Catalyst-Controlled Selectivity in the Synthesis of C2- and C3-Sulfonate Esters from Quinoline N-Oxides and Aryl Sulfonyl Chlorides
The first example of the catalyst-controlled selective synthesis of C2- and C3-sulfonate-ester-substituted quinolines was developed by employing LaCl3 and chitosan@CuI catalysts, respectively. This protocol provides an expeditious route to an important class of quinoline derivatives frequently found in many biologically active compounds and features good practicality, high efficiency, and environmental friendliness. In addition, the easily recoverable chitosan@copper catalysts can be recycled five times without significant loss of catalytic performance.
Ying, Beibei,Xu, Jun,Zhu, Xiaolei,Shen, Chao,Zhang, Pengfei
p. 2604 - 2608
(2016/08/30)

QUINOLONES AS INHIBITORS OF CLASS IV BROMODOMAIN PROTEINS
The present invention provides compounds of formula (I) as described herein and pharmaceutically acceptable salts, hydrates and solvates thereof for use in medicine, for example in the treatment of acute myeloid leukaemia:
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Page/Page column 55

(2016/03/19)

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral
The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.
Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Wang, Lei,He, Yun-Qi,Ye, Jian-Heng,Li, Jing,Zhi, Yong-Gang,Yu, Da-Gang
supporting information
p. 7068 - 7072
(2016/07/06)

Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
A high-yielding and practical method for the synthesis of phenols from electron-deficient haloarenes and heteroarenes has been developed. The products are formed from acetohydroxamic acid as the hydroxide source via a novel SNAr reaction/Lossen rearrangement sequence. Notably, these reactions employ inexpensive and air-stable reagents, require no special handling, occur under mildly basic conditions, and form products in high yields in the presence of electrophilic and protic functionality. The utility of this methodology is demonstrated by the high-yielding hydroxylation of two base-sensitive complex substrates.
Fier, Patrick S.,Maloney, Kevin M.
supporting information
p. 2244 - 2247
(2016/06/01)

Quinoline derivatives and their use
The invention discloses a quinoline derivative and a usage thereof, a compound with a structure as shown in a formula (I) and or a pharmaceutically acceptable salt of the compound. The compound or the pharmaceutically acceptable salt thereof disclosed by the invention can be applied to the field of preparation of drugs for preventing or treating tumors.
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Paragraph 0099-0101; 0147; 0148; 0162; 0163

(2017/03/14)

Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Matheny, Jonathon P.,Rubin, Michael
p. 8647 - 8656
(2015/03/03)

Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
Quinolinone derivatives were constructed via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.
Wu, Junliang,Xiang, Shaohua,Zeng, Jing,Leow, Minli,Liu, Xue-Wei
supporting information
p. 222 - 225
(2015/01/30)

METHOD OF PRODUCING NITROGEN-CONTAINING HETEROCYCLIC COMPOUND
PROBLEM TO BE SOLVED: To provide a chemical compound production method realizing easy and high-yield production of a nitrogen-containing heterocyclic compound useful as a synthetic intermediate and the like in many fields such as medicine, agriculture and synthetic resin additives. SOLUTION: In the production method, an ortho-substituted benzene azide derivative represented by formula (1) is reacted with carbon dioxide in the presence of a reductant to obtain a compound represented by formula (2). [R is H and/or a substituent; A is an intramolecular cyclizable group; and B is a divalent linking group of C, N and O. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0045

(2016/10/08)

Functionalization of a Pyridine Framework through Intramolecular Reissert-Henze Reaction of N-(Carbamoyloxy)pyridinium Salts and Unexpected Insertion of Ethereal Solvents
A new strategy for synthesis of the 2-pyridyl carbamates is reported. This strategy exploits a new intramolecular transformation of an acyloxy group from N-carbamoyloxypyridinium salts (Reissert-Henze-type reaction) as the key step. Addition of a silver salt effectively accelerates the intramolecular attack of the carbonyl oxygen at the 2-position of the pyridine ring. Additionally, a new rearrangement of the acyloxy group, combined with insertion of an ethereal solvent to give pyridine derivatives having a coordinating tether, is reported. A new strategy that gives 2-pyridyl carbamates upon treatment of N-(carbamoyloxy)pyridinium salts with silver oxide is reported. Additionally, a new rearrangement of the acyloxy group, combined with insertion of an ethereal solvent to give pyridine derivatives with a coordinating tether, is reported.
Asahara, Haruyasu,Kataoka, Asuka,Hirao, Shotaro,Nishiwaki, Nagatoshi
p. 3994 - 3999
(2015/06/30)

Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides
Novel fluorescent quinoxaline and quinoline hydroperoxides were shown to perform dual role as both fluorophores for cell imaging and photoinduced DNA cleaving agents. Photophysical studies of newly synthesized quinoxaline and quinoline hydroperoxides showed that they all exhibited moderate to good fluorescence. Photolysis of quinoxaline and quinoline hydroperoxides in acetonitrile using UV light above 350 nm resulted in the formation of corresponding ester compounds via γ-hydrogen abstraction by excited carbonyl chromophore. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroperoxides by UV light (≥350 nm). Both hydroxyl radicals and singlet oxygen were identified as reactive oxygen species (ROS) responsible for the DNA cleavage. Further, we showed quinoline hydroperoxide binds to ct-DNA via intercalative mode. In vitro biological studies revealed that quinoline hydroperoxide has good biocompatibility, cellular uptake property and cell imaging ability. Finally, we showed that quinoline hydroperoxide can permeate into cells efficiently and may cause cytotoxicity upon irradiation by UV light.
Chowdhury, Nilanjana,Gangopadhyay, Moumita,Karthik,Pradeep Singh,Baidya, Mithu,Ghosh
p. 188 - 198
(2014/01/06)

Manganese(III)-mediated direct Csp2-H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate
Mn(OAc)3-mediated direct Csp2-H radical trifluoromethylation of coumarins with CF3SO2Na (Langlois reagent) to afford selective 3-trifluoromethyl coumarins in moderate to good yields is described. This methodology can also be applied to the trifluoromethylation of quinolinones and pyrimidinones. The Royal Society of Chemistry 2014.
Cao, Xiao-Hui,Pan, Xiangqiang,Zhou, Peng-Jun,Zou, Jian-Ping,Asekun, Olayinka Taiwo
supporting information
p. 3359 - 3362
(2014/03/21)

Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Bijieva, Asiyat S.,Rubin, Michael
supporting information
p. 9786 - 9788
(2014/12/12)

Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones
A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines
Manikandan, Rajendran,Jeganmohan, Masilamani
supporting information
p. 3568 - 3571
(2014/07/21)

A Pd-Catalyzed one-pot dehydrogenative aromatization and ortho-functionalization sequence of N-acetyl enamides
The one-pot dehydrogenation and ortho-functionalization sequence provides access to highly functionalized arylamine-containing derivatives from readily accessible cyclic N-acetyl enamides. The Royal Society of Chemistry 2014.
Kim, Jinhee,Moon, Youngtaek,Lee, Suhyun,Hong, Sungwoo
p. 3227 - 3230
(2014/03/21)

Synthesis, photophysical properties, and application of o - And p -amino green fluorescence protein synthetic chromophores
The o- and p-amino green-fluorescence-protein synthetic chromophores (GFPSCs) were synthesized from the corresponding o- and p-nitro protecting group. Among the four protecting groups of the o-amino group, the o-nitro protecting group is the only choice to synthesize the o-amino GFPSCs. The first singlet excited states of o- and p-amino GFPSCs carry significant charge-transfer character through the mechanism of photoinduced charge transfer (PCT). The o-amino GFPSCs can serve as wavelength-ratiometric fluorescence sensors that selectively recognize Cr3+ in aqueous medium through a PCT mechanism.
Chen, Yi-Hui,Lo, Wei-Jen,Sung, Kuangsen
p. 301 - 310
(2013/02/25)

Synthesis of the N-substituted pyridin-1(2H)-one framework by ligand-assisted Pd-catalyzed reactions
An efficient Pd-catalyzed method for the synthesis of N-substituted pyridin-1(2H)-ones was developed. The corresponding derivatives, which can be found in numerous biologically active compounds, were obtained in good to excellent yields. A possible mechanism for this reaction is discussed. An efficient ligand-assisted palladium-catalyzed approach for the straightforward synthesis of the pyridin-2(1H)-one framework was developed. This method provides one of the easiest pathways to access this class of valuable compounds from easily available starting materials (2-chloropyridines). A possible mechanism for this reaction is discussed. Copyright
Zhou, Kang,Wen, Ping,Chen, Wenlin,Ma, Chaowei,Huang, Guosheng
supporting information
p. 448 - 452
(2013/02/25)

Acceptorless dehydrogenation of C-C single bonds adjacent to functional groups by metal-ligand cooperation
Unprecedented direct acceptorless dehydrogenation of C-C single bonds adjacent to functional groups to form α,β-unsaturated compounds has been accomplished by using a new class of group 9 metal complexes. Metal-ligand cooperation operated by the hydroxycyclopentadienyl ligand was proposed to play a major role in the catalytic transformation.
Kusumoto, Shuhei,Akiyama, Midori,Nozaki, Kyoko
supporting information
p. 18726 - 18729
(2014/01/06)

Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).
Sridhar Reddy, Maddi,Thirupathi, Nuligonda,Babu, Madala Hari
p. 5803 - 5809
(2012/11/07)

Palladium-catalyzed intermolecular domino reaction of gem-dibromoenynes with anilines; A one-pot synthesis of quinolines and quinolinones
An efficient domino process involving palladium-catalyzed amination of an alkenyl bromide, 1,5-H transfer, annulation via 6-exo-dig electrophilic cyclization, and palladium-catalyzed etherification, is described. This reaction provides an efficient one-pot synthesis of multi-substituted quinolines and quinolinones from gem-dibromoenynes and anilines. Georg Thieme Verlag Stuttgart New York.
Meng, Tianhao,Zhang, Wen-Xiong,Zhang, Hui-Jun,Liang, Yun,Xi, Zhenfeng
p. 2754 - 2762
(2012/11/07)

Development of 1-Hydroxy-2(1H)-quinolone-Based Photoacid Generators and Photoresponsive Polymer Surfaces
A new class of carboxylate and sulfonate esters of 1-hydroxy-2(1H)- quinolone has been demonstrated as nonionic photoacid generators (PAGs). Irradiation of carboxylates and sulfonates of 1-hydroxy-2(1H)-quinolone by UV light (γ≥310 nm) resulted in homolysis of weak N-O bond leading to efficient generation of carboxylic and sulfonic acids, respectively. The mechanism for the homolytic N-O bond cleavage was supported by time-dependent DFT calculations. Photoresponsive 1-(p-styrenesulfonyloxy)-2-quinolone-methyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolone-lauryl acrylate (SSQL-LA) copolymers were synthesized from PAG monomer 1-(p-styrenesulfonyloxy) -2-quinolone, and subsequently controlled surface wettability was demonstrated for the above-mentioned photoresponsive polymers. Copyright
Ikbal, Mohammed,Banerjee, Rakesh,Atta, Sanghamitra,Jana, Avijit,Dhara, Dibakar,Anoop, Anakuthil,Singh, N. D. Pradeep
p. 11968 - 11975
(2012/10/29)

Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbonoxygen bonds
Ni(0)/NHC-based catalyst system can promote the amination of N-heteroaryl methyl ethers via the cleavage of normally unreactive carbon-oxygen bonds. Electron-deficient N-heteroarenes including pyridine, quinoline, isoquinoline, and quinoxaline undergo amination to afford aminopyridine and related heteroarenes, which constitute an important class of compounds.
Tobisu, Mamoru,Yasutome, Ayaka,Yamakawa, Ken,Shimasaki, Toshiaki,Chatani, Naoto
supporting information; experimental part
p. 5157 - 5161
(2012/07/31)

A practical, one-pot synthesis of sulfonylated pyridines
A concise and efficient one-pot synthesis of functionalized sulfonylated pyridines via an SNAr reaction of readily available pyridines and sodium sulfinate salts in the presence of tetrabutylammonium chloride is presented.
Maloney, Kevin M.,Kuethe, Jeffrey T.,Linn, Kathleen
supporting information; experimental part
p. 102 - 105
(2011/03/19)

Dehalogenation and barbier-type hydroxyalkylation of π-deficient haloheterocycles using indium
The reaction of π-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of α-iodoheterocycles with indium in the presence of pivalaldehyde.
Fukuda, Eri,Takahashi, Yukiko,Hirasawa, Natsumi,Sugimoto, Osamu,Tanji, Ken-Ichi
experimental part
p. 1163 - 1170
(2010/10/03)