cas 5470-96-2, 2-Quinolinecarboxaldehyde | Articles data

Articles about 5470-96-2Total 82 be found

Article title
Article abstract
Author
Journal number and time
Download

STIMULI - OR BIO- RESPONSIVE COPOLYMERS, THE POLYMERSOMES COMPRISING THE SAME AND THEIR USE IN DRUG DELIVERY
The present invention concerns amphiphilic copolymers that may be photo- or redox-cleavable and that may assemble into polymersomes. It also concerns their process of preparation and their use as drug carriers.
-
Page/Page column 28

(2021/06/22)

A Metal- and Azide-free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5-a]quinolines and their Application to Construct C?C and C-P Bonds, 2-Cyclopropylquinolines and Imidazo[1,5-a]quinolines
An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5-a]quinolines from methyl azaarenes and N-tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram-scale. 1,2,3-Triazoles are an important skeletal structure for the construction of C?C and C?P bonds, 2-cyclopropylquinolines and imidazo[1,5-a]quinolines, for which different synthetic applications were explored. (Figure presented.).
Shang, Zhi-Hao,Zhang, Zhen-Xiao,Weng, Wei-Zhao,Wang, Yu-Fei,Cheng, Tian-Wei,Zhang, Qiu-Yi,Song, Li-Qun,Shao, Tian-Qi,Liu, Kai-Xuan,Zhu, Yan-Ping
supporting information
p. 490 - 496
(2020/12/07)

Iodine-Catalyzed Construction of Dihydrooxepines via 3-Methyl-5-Pyrazolones C?H Oxidation/Functionalization of Quinolines Cascade
An efficient iodine-catalyzed [3+3+1] annulation for the construction of dihydrooxepine scaffolds with quinoline units was developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and pharmaceutical molecules.
Zhang, Rong,Wang, Jun,Jin, Weiwei,Zhang, Yonghong,Wang, Bin,Xia, Yu,Liu, Chenjiang
supporting information
p. 3807 - 3811
(2021/08/24)

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.
Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin
supporting information
p. 7445 - 7449
(2021/10/02)

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer
Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.
Wang, Ao,Wang, Yawan,Meng, Xin,Yang, Yushe
(2021/01/07)

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes
A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.
Zhou, Tongtong,He, Xinwei,Zuo, Youpeng,Wu, Yuhao,Hu, Wangcheng,Zhang, Shiwen,Duan, Jiahui,Shang, Yongjia
p. 621 - 626
(2021/02/12)

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System
An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.
Hu, Qi-Qi,Gao, Yan-Ting,Sun, Jia-Chen,Gao, Jing-Jing,Mu, Hong-Xiao,Li, Yi-Ming,Zheng, Ya-Nan,Yang, Kai-Rui,Zhu, Yan-Ping
supporting information
p. 9000 - 9005
(2021/11/24)

Iodine-Promoted Synthesis of Dipyrazolo/Diuracil-Fused Pyridines and o-Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4-Methylazaarenes
The iodine-promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene-substituted bis-pyrazolo[3,4-b:4′,3′-e]pyridines (BPPs), diuracilpyridines and o-amino diheteroaryl ketones. The domino procedure proceeded with easily available methyl azaarenes, 5-aminouracils and substituted 5-aminopyrazoles. This protocol is a simple and metal-free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil-fused pyridines on a gram scale. (Figure presented.).
Zhang, Xin-Ke,Miao, Xiao-Yu,Jiang, Hui-Ru,Ge, Fei,Sun, Jia-Chen,Zhang, Rui-Ying,Ouyang, Qin,Fan, Wei-Yu,Zhu, Yan-Ping,Sun, Yuan-Yuan
p. 4632 - 4638
(2021/08/30)

Methanol as a formylating agent in nitrogen heterocycles
A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylating reagent. It effectively solved the long-standing problems associated with using methanol as a formylating reagent in these types of reactions. Compared to the traditional Minisci C-H formylation methods, this protocol is highly atom-economical, simple to operate, and environmentally friendly and shows good functional group tolerance. This Minisci formylation strategy is a straightforward approach for the late-stage functionalization of N-heteroarenes. This journal is
Xu, Zhengbao,Zhang, Lizhi
p. 9476 - 9482
(2021/11/17)

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics
Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.
Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Gutiérrez-De-Terán, Hugo,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui
p. 12938 - 12963
(2021/09/11)

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides
An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.
Shang, Zhi-Hao,Sun, Ji-Na,Guo, Jiang-Shan,Sun, Yuan-Yuan,Weng, Wei-Zhao,Zhang, Zhen-Xiao,Li, Zeng-Jing,Zhu, Yan-Ping
supporting information

(2020/01/08)

Development and characterization of BODIPY-derived tracers for fluorescent labeling of the endoplasmic reticulum
Visualization of the structure of the Endoplasmic Reticulum (ER) in living cells is important for the understanding of its function. Here we synthesized a library of 8 BODIPY labeledhydroxyquinoline derivatives and evaluated their spectroscopic properties, cytotoxicity, and intracellular localization. The compounds were easily obtained in 34–80% yield. Based on the spectral properties and low cytotoxicity, we selected the quinolin-8-yl pentanoate derivative 17 for in vivo labeling of the ER. Fluorescence staining of the ER was evaluated by comparison with a commercial ER tracker. The molecules here developed are smaller than the alternatives commercially available while still presenting a high specificity towards the ER.
Daelemans, Brent,Dehaen, Wim,Manshian, Bella,Pokorny, Jan,Rocha, Susana,Silveira-Dorta, Gaston,Soenen, Stefaan,Startek, Justyna B.,Van der Auweraer, Mark,Vandaele, Johannes,de Jong, Flip
(2020/01/28)

I2/K2S2O8 Mediated Direct Oxidative Annulation of Alkylazaarenes with Amidines for the Synthesis of Substituted 1,3,5-Triazines
A direct method for the synthesis of heteroaryl-substituted 1,3,5-triazines from readily available methyl-azaarenes and amidines has been developed. The present method involves iodine mediated cascade aerobic C(sp3)–H oxidative amination and following condensation, cyclization with amidine. Both of methyl quinoline, pyridine and benzothiazole derivatives could be well tolerated to react with various amidines leading to corresponding products in good to excellent yields.
Zhang, Jun,Zheng, Tingting,Zhang, Jidong
supporting information
p. 860 - 865
(2020/02/20)

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
Aleku, Godwin A.,Leys, David,Roberts, George W.
p. 3927 - 3939
(2020/07/09)

Photoredox-Catalyzed Redox-Neutral Minisci C?H Formylation of N-Heteroarenes
We report a protocol for redox-neutral Minisci C?H formylation of N-heteroarenes using 1,3-dioxoisoindolin-2-yl 2,2-diethoxyacetate as a formyl equivalent at room temperature. This scalable benchtop protocol offers a distinct advantage over traditional reductive carbonylation and Minisci C?H formylation methods in not requiring the use of carbon monoxide, pressurized gas, a stoichiometric reductant, or a stoichiometric oxidant. (Figure presented.).
Dong, Jianyang,Wang, Xiaochen,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information
p. 2155 - 2159
(2020/02/11)

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes
A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.
Ye, Rongzi,Cao, Yuanjie,Xi, Xiaoxiang,Liu, Long,Chen, Tieqiao
supporting information
p. 4220 - 4224
(2019/05/10)

Oxidative C(sp3)-H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3-a]pyridines
We herein describe an oxidative [4 + 1] annulation used to prepare 1,2,4-triazolo[4,3-a]pyridines in the presence of I2-DMSO. This protocol enables synthesis of triazolo[4,3-a]pyridine-quinoline linked diheterocycles via a direct oxidative functionalization of sp3 C-H bonds of 2-methyl-azaheteroarenes. The reaction shows a wide substrate scope and good functional group tolerance.
Weng, Wei-Zhao,Gao, Yin-He,Zhang, Xue,Liu, Yan-Hua,Shen, Ying-Jie,Zhu, Yan-Ping,Sun, Yuan-Yuan,Meng, Qing-Guo,Wu, An-Xin
supporting information
p. 2087 - 2091
(2019/02/27)

Consecutive Intermolecular Reductive Amination/Asymmetric Hydrogenation: Facile Access to Sterically Tunable Chiral Vicinal Diamines and N-Heterocyclic Carbenes
A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. A broad range of sterically tunable chiral N,N′-diaryl vicinal diamines were obtained in high yields (up to 95 %) with excellent enantioselectivity (up to >99 % ee). The resulting chiral diamines could be readily transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki–Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis, respectively.
Chen, Ya,Pan, Yixiao,He, Yan-Mei,Fan, Qing-Hua
supporting information
p. 16831 - 16834
(2019/11/13)

Copper-catalyzed three-component reaction of: N-heteroaryl aldehydes, nitriles, and water
An efficient and straightforward method for the synthesis of N-heteroaroyl imides has been successfully developed involving a copper-catalyzed radical-triggered three-component reaction of N-heteroaryl aldehydes, nitriles, and water. Mechanistic studies indicate that the reaction may undergo a radical-triggered Ritter-type reaction in which water serves as the oxygen source for the formation of the C-O bond. The reaction has advantages such as a broad substrate scope for the N-heteroaryl aldehydes, atom economy, and simple operation.
Bao, Hanyang,Zhou, Bingwei,Jin, Hongwei,Liu, Yunkui
p. 5021 - 5028
(2019/06/03)

Antiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline–hydrazone hybrids
The application of antiaging agents can contribute to the prevention and control of skin photoaging. In the current research, nine quinoline–hydrazone hybrids were synthesized to obtain biologically active compounds as possible antiaging agents. The compounds were tested through a comprehensive in vitro evaluation of antielastase, anticollagenase, and antihyaluronidase activities along with the determination of their potential to quench reactive oxygen species (ROS) by the ORAC method. The selected hybrids were subsequently tested on human dermal fibroblasts (HDF) to reveal possible UVB photoprotective activity. The most potent antiaging protection of all the prepared compounds was shown by the trihydroxylated quinoline–hydrazones 5 and 9, which showed the best collagenase inhibition (IC50 = 39.4 and 45.6 μM, respectively). Compound 5 also showed activity against elastase and hyaluronidase (IC50 = 164.2 and 318.8 μM, respectively). The molecular docking results suggest that the difference of inhibition between 5 and 9 is principally attributed to the hydrogen bonds interactions in the residues His218 and His228, and Zn atom in collagenase, Val216 in elastase and Tyr75 in hyaluronidase. In addition, compounds 5 and 9 were able to significantly protect human skin cells from UVB radiation in vitro. These compounds significantly decreased UVB-induced MMP-1 and ROS production and inhibited the suppression of type I procollagen synthesis in cultured HDF. The in silico dermatopharmacokinetic parameters showed promising results. Therefore, our study presented promising results for antiaging drug discovery, focusing on quinoline–hydrazone hybrids as dual inhibitors of skin aging-related enzymes, antioxidants, and inhibitors of the biological effects of UVB irradiation.
Osorio, Edison,Bravo, Karent,Cardona, Wilson,Yepes, Andres,Osorio, Edison H.,Coa, Juan C.
p. 1959 - 1973
(2019/09/03)

Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds: Via sp3 C-H functionalization of azaarenes
An efficient iodine-mediated one-pot synthetic protocol for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C-H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions and high yields, making this protocol an attractive strategy towards the synthesis of bioactive molecules and their key building blocks.
Mani, Geeta Sai,Donthiboina, Kavitha,Shankaraiah, Nagula,Kamal, Ahmed
p. 15999 - 16006
(2019/10/28)

Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds
A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.
Gao, Xianying,Han, Shuaijun,Zheng, Maolin,Liang, Apeng,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie,Li, Jingya
p. 4040 - 4049
(2019/04/30)

Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation
The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.
Xue, Yu,He, Xiaomeng,Yang, Taoyi,Wang, Yuxi,Liu, Zhenming,Zhang, Guisen,Wang, Yanxing,Wang, Kewei,Zhang, Liangren,Zhang, Lihe
(2019/08/20)

Oxidative sp3 C–H Functionalization of Methyl Substituted Aza-Aromatics: An Easy Access to N-Fused Polyheterocycles
An efficient metal-free, one-pot strategy has been developed for the synthesis of diverse N-fused polyheterocycles such as pyrido-/thiazolo-/benzthiazolo-imidazo[4,5-c]quinolines and indolo-/pyrrolo-[1,2-a]quinoxalines mediated by I2/DMSO in the presence of 10 mol-% TBHP. This protocol involves a cascade sequence of oxidative imination/cyclization/aromatization reactions through sp3 C–H functionalization of methyl-substituted aza-aromatics with a variety of arylamine conjugated heterocycles by means of modified Pictet–Spengler type cyclization. The advantage of the present method includes environmentally benign, atom economy, and mild reaction conditions resulting in various N-fused polyheterocycles.
Sridevi, Bhima,Reddy Kandimalla, Satheeshkumar,Subba Reddy
p. 6800 - 6806
(2019/11/11)

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant
A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).
Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
supporting information
p. 2262 - 2267
(2019/04/17)

KOTBu-promoted oxidative dimerizations of 2-methylquinolines to 2-alkenyl bisquinolines with molecular oxygen
KOtBu-promoted oxidative dimerizations of 2-methylquinolines with molecular oxygen as the oxidant have been developed for the first time. The mild reaction conditions allow the homo- and cross-dimerizations of 2-methylquinolines to give functionalized 2-alkenyl bisquinolines in highly trans-selective manners.
Wang, Zhen,Zhang, Jinjin,Shi, Jianxue,Wang, Huiqiao
p. 30139 - 30143
(2019/10/04)

The synthesis of imidazo[1,5-a]quinolines via a decarboxylative cyclization under metal-free conditions
An iodine-mediated decarboxylative cyclization was developed from α-amino acids and 2-methyl quinolines under metal-free conditions, affording a variety of imidazo[1,5-a]quinolines with moderate to good yields.
Yan, Zicong,Wan, Changfeng,Yang, Yu,Zha, Zhenggen,Wang, Zhiyong
p. 23058 - 23065
(2018/07/10)

Synthesis of Imidazo[1,5- a ]quinolines via Metal-Free Oxidative Amination of sp 3 C-H Bonds
A novel oxidative amination of sp 3 C-H bonds was developed for the efficient synthesis of imidazo[1,5- a ]quinolines from readily available α-amino acids and (2-azaaryl)methanes. This domino protocol, which was established in a TBAI-TBHP oxidation system, includes transition-metal-free decarboxylation and intramolecular cyclization. This method represented a new avenue for the synthesis of N-heterocycles using 2-methylquinolines as the synthon of quinoline-2-carbaldehydes.
Liu, Huanhuan,Wang, Xinfeng,Ma, Chen
p. 2761 - 2767
(2018/06/08)

Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
Iodine-promoted oxidative C-H/C-H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C-H functionalization rather than the N-H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.
Rahim, Abdul,Shaik, Siddiq Pasha,Baig, Mirza Feroz,Alarifi, Abdullah,Kamal, Ahmed
p. 635 - 644
(2018/02/07)

SQUARYLIUM COMPOUNDS AND INFRARED CUT FILMS, INFRARED CUT FILTERS AND ELECTRONIC DEVICES INCLUDING THE SAME
A squarylium compound has high transmittance in a visible wavelength spectrum of light and is configured to selectively absorb light in an infrared/near infrared wavelength spectrum of light.
-
Paragraph 0401; 0402

(2018/10/21)

Unprecedented Reaction Pathway of Sterically Crowded Calcium Complexes: Sequential C?N Bond Cleavage Reactions Induced by C?H Bond Activations
Five bis(quinolylmethyl)-(1H-indolylmethyl)amine (BQIA) compounds, that is, {(quinol-8-yl-CH2)2NCH2(3-Br-1H-indol-2-yl)} (L1H) and {[(8-R3-quinol-2-yl)CH2]2NCH(R2)[3-R1-1H-indol-2-yl]} (L2–5H) (L2H: R1=Br, R2=H, R3=H; L3H: R1=Br, R2=H, R3=iPr; L4H: R1=H, R2=CH3, R3=iPr; L5H: R1=H, R2=nBu, R3=iPr) were synthesized and used to prepare calcium complexes. The reactions of L1–5H with silylamido calcium precursors (Ca[N(SiMe2R)2]2(THF)2, R=Me or H) at room temperature gave heteroleptic products (L1, 2)CaN(SiMe3)2 (1, 2), (L3, 4)CaN(SiHMe2)2 (3 a, 4 a) and homoleptic complexes (L3, 5)2Ca (D3, D5). NMR and X-ray analyses proved that these calcium complexes were stabilized through Ca???C?Si, Ca???H?Si or Ca???H?C agostic interactions. Unexpectedly, calcium complexes ((L3–5)CaN(SiMe3)2) bearing more sterically encumbered ligands of the same type were extremely unstable and underwent C?N bond cleavage processes as a consequence of intramolecular C?H bond activation, leading to the exclusive formation of (E)-1,2-bis(8-isopropylquinol-2-yl)ethane.
Yang, Yang,Wang, Haobing,Ma, Haiyan
supporting information
p. 239 - 247
(2017/02/05)

N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds
A one-pot protocol for the synthesis of structurally diverse 2-hetarylbenzothiazoles via oxidative condensation of the sp3 C-H bond with benzothiazoles has been described. This process is metal free and operationally simple. A series of 2-hetarylbenzothiazoles were prepared in moderate to good yield under mild conditions.
Chu, Xianglong,Duan, Tiantian,Liu, Xuan,Feng, Lei,Jia, Jiong,Ma, Chen
p. 1606 - 1611
(2017/02/23)

A facile I2-catalyzed synthesis of imidazo[1,2-: A] pyridines via sp3 C-H functionalization of azaarenes and evaluation of anticancer activity
A facile and efficient metal-free, one-pot, three component synthetic protocol has been developed for the synthesis of medicinally important substituted imidazo[1,2-a]pyridines via the iodine-catalysed oxidative amination of benzylic C-H bonds of azaarenes with 2-aminoazines and condensation with isocyanides. The presented methodology offers the advantages of wide substrate scope, moderate reaction conditions, environment friendliness, clean and simple protocol with high atom economy apart from higher yields. The synthesized compounds were screened for their anti-cancer activity in selected human cancer cell lines. Compounds 4a, 4b, 4c, 4i, 7a, 7b and 7m have significant IC50 values ranging from 4.88 ± 0.28 to 14.55 ± 0.74 μM.
Mani, Geeta Sai,Shaik, Siddiq Pasha,Tangella, Yellaiah,Bale, Swarna,Godugu, Chandraiah,Kamal, Ahmed
p. 6780 - 6791
(2017/08/22)

Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole
An efficient one-pot synthetic procedure has been developed for the preparation of heteroarenyl-benzimidazoles via oxidative Csp3-H functionalization with o-phenylenediamine using I2-DMSO in open air from easily available starting materials. Based on a logical plan a spectrum of multi fundamental reactions like iodination, Kornblum oxidation and amination were brought into one-pot. By using this simple method a library of heteroarenyl-benzimidazoles derivatives (3a–t and 5a–g) and heteroarenyl-benzothiazole (3u) have been synthesized in good to excellent yield and screened for their cytotoxicity against a group of four human cancer cell lines. Among them 3h, 3q and 5b showed significant cytotoxic activities with an IC50 of 1.69, 1.62 and 2.81 μM respectively against lung cancer (A549) cell line.[Figure presented]
Baig, Mirza Feroz,Shaik, Siddiq Pasha,Nayak, V. Lakshma,Alarifi, Abdullah,Kamal, Ahmed
supporting information
p. 4039 - 4043
(2017/08/23)

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction
The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.
Diaz-Mu?oz, Gaspar,Isidorio, Raquel Geralda,Miranda, Izabel Luzia,de Souza Dias, Gabriel Nunes,Diaz, Marisa Alves Nogueira
supporting information
p. 3311 - 3315
(2017/07/27)

Metal-free C(sp3)–H oxidation of 2-methylquinolines with PIDA under microwave irradiation
An efficient metal-free protocol has been developed for the sp3C–H bond oxidation of 2-methylquinolines in the presence of PIDA under microwave irradiation, providing 2-quinolinecarboxaldehydes with moderate to high yields and excellent selectivities. A wide range of 2-quinolinecarboxaldehydes with different functional groups have been synthesized. A tentative mechanism has been presented to explain this highly selective oxidation process.
Jiang, Long,Huang, Yingyi,Yan, Yiyan,Xie, Yuanyuan
supporting information
p. 4149 - 4151
(2016/08/24)

Copper-Catalyzed Aerobic Oxidation of Azinylmethanes for Access to Trifluoromethylazinylols
A copper-catalyzed oxygenation of methylazaarenes was found to occur in the absence of both ligand and additive, and has been successfully employed for the synthesis of trifluoromethylazinylketols. This synthetic strategy incorporates aerobic oxidation and a trifluoromethylation in one-pot and provides a novel method for the trifluoromethylation of aliphatic C-H bond.
Zheng, Gang,Liu, Hao,Wang, Mang
supporting information
p. 519 - 523
(2016/06/01)

Chemical synthesis method of quinoline (oxaline)-2-carboxaldehyde compounds
The invention relates to a preparation method of quinoline (oxaline)-2-carboxaldehyde compounds. The preparation method comprises the following steps of dissolving 2-methylquinoline(oxaline) shown in a formula (II) into an organic solvent, adding iron salts, and completely reacting under the condition of 100 to 180DEG C with the assistance of microwave; performing after treatment on a reaction solution to obtain the quinoline (oxaline)-2-carboxaldehyde compounds shown in a formula (I), wherein the feed molar ratio of the iron salts to the quinoline (oxaline)-2-carboxaldehyde compounds is (0.5 to 3.5):1. R in the formula (I) and the formula (II) is hydrogen at the same time; or the hydrogen is monosubstituted or polysubstituted by alkyls of C1 to C8, alkoxys of C1 to C8, nitryl or halogen; the number of substituent groups is n; X in the formula (I) and the formula (II) is carbon or nitrogen at the same time. The preparation method disclosed by the invention has the advantages of short reaction time, low reaction temperature, wide application range of reaction, good reaction selectivity, low price and no toxicity of a used catalyst, and simplicity and convenience in operation; the preparation method meets the requirement of green chemistry. (The formulas are shown in the description).
-
Paragraph 0028-0030

(2017/04/14)

Catalytic Aerobic Photo-oxidation of a Methyl Group on a Heterocycle to Produce an Aldehyde via Homolytic C-I Bond Cleavage caused by Irradiation with Visible Light
A new catalytic method was developed for photo-oxidizing the methyl group on aromatic heterocycles such as benzothiazole, benzoxazole, and quinoline to produce the corresponding aldehyde. This is the first report of the metal-free catalytic synthesis of benzothiazole-2-carboxaldehydes using molecular oxygen as the terminal oxidant.
Nagasawa,Tachikawa,Yamaguchi,Tada,Miura,Itoh
supporting information
p. 178 - 182
(2016/02/14)

Evaluation of some quinoline-based hydrazone derivatives as insecticidal agents
In continuation of our program aimed at the discovery and development of efficient insecticidal agents, a series of quinoline-based hydrazone derivatives were synthesized and evaluated as insecticidal agents against three-day-old larvae of Spodoptera litura (Noctuidae: Lepidoptera), a polyphagous insect pest of many important crops, in vivo at 1 mg mL1. In particular, compounds 3c, 3e, 4g, 4h, and 6f showed potent insecticidal activity with 7 day mortality rates greater than 93%, and were comparable to that of the positive control toosendanin.
Yu, Xiang,Feng, Gang,Huang, Jiulin,Xu, Hui
p. 30405 - 30411
(2019/01/14)

Copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols
Efficient copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols has been developed. A variety of N-heteroaryl esters including those with functional groups are produced in good to excellent yields under the present reaction conditions.
Liu, Min,Chen, Tieqiao,Yin, Shuang-Feng
p. 690 - 693
(2016/02/18)

Aerobic Copper-Catalyzed Halocyclization of Methyl N-Heteroaromatics with Aliphatic Amines: Access to Functionalized Imidazo-Fused N-Heterocycles
A new aerobic copper-catalyzed halocyclization reaction of methyl N-heteroaromatics and aliphatic amines has been developed, which enables straightforward access to functionalized imidazo-fused N-heterocycles with the merits of good functional tolerance, use of easily available copper salts as the catalysts, lithium halides as the halogen sources, and O2 as a sole oxidant. Due to the reaction features' selective introduction of halogen functionalities to the newly formed imidazo ring, further extensions of the developed chemistry toward synthetic diversity, including effective access to functional materials, are easily envisioned.
Tan, Zhenda,Zhao, He,Zhou, Changjian,Jiang, Huanfeng,Zhang, Min
p. 9939 - 9946
(2016/11/02)

Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids
Abstract Cutaneous leishmaniasis and Chagas disease are vector-borne parasitic disease causing serious risks to million people living in poverty-stricken areas. Both diseases are a major health problem in Latin America, and currently drugs for the effective treatment of these diseases have important concerns related with efficacy or toxicity than need to be addressed.We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal and trypanocidal activities) of ten quinolone-hydrazone hybrids. The structure of the products was elucidated by spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis which is the most prevalent Leishmania species in Colombia and Trypanosoma cruzi that is the major pathogenic species to humans; in turn, cytotoxicity was evaluated against human U-937 macrophages.Compounds 6b, 6c and 8 showed activity against L. (V) panamensis with EC50 of 6.5 ± 0.8 μg/mL (21.2 μM), 0.8 ± 0.0 μg/mL (2.6 μM) and 3.4 ± 0.6 μg/mL (11.1 μM), respectively, while compounds 6a and 6c had activity against T. cruzi. with EC50 values of 1.4 ± 0.3 μg/mL (4.8 μM) and 6.6 ± 0.3 μg/mL (4.6 μM), respectively. Even compound 6a showed better activity against T. cruzi than the standard drug benznidazole with EC50 Combining double low line 10.5 ± 1.8 μg/mL (40.3 μM).Analysis of the results obtained against leishmaniasis indicates that antiparasite activity is related to the presence of 2-substituted quinoline (isoquinolinic core) and the hydroxyl group in positions 3 and 4 of the aromatic ring. Although the majority of these compounds were highly cytotoxic, the antiparasite activity was higher than cytotoxicity and therefore, they still have potential to be considered as hit molecules for leishmanicidal and trypanocidal drug development.
Coa, Juan Carlos,Castrillón, Wilson,Cardona, Wilson,Carda, Miguel,Ospina, Victoria,Mu?oz, July Andrea,Vélez, Iván D.,Robledo, Sara M.
p. 746 - 753
(2015/08/06)

Acid-Activatable Michael-Type Fluorescent Probes for Thiols and for Labeling Lysosomes in Live Cells
A Michael addition is usually taken as a base-catalyzed reaction. Most fluorescent probes have been designed to detect thiols in slightly alkaline solutions (pH 7-9). The sensing reactions of almost all Michael-type fluorescent probes for thiols are faster in a high pH solution than in a low pH solution. In this work, we synthesized a series of 7-substituted 2-(quinolin-2-ylmethylene)malonic acids (QMAs, substituents: NEt2, OH, H, Cl, or NO2) and their ethyl esters (QMEs) as Michael-type fluorescent probes for thiols. The sensing reactions of QMAs and QMEs occur in distinct pH ranges, pH 7 for QMEs. On the basis of experimental and theoretic studies, we have clarified the distinct pH effects on the sensing reactivity between QMAs and QMEs and demonstrated that two QMAs (NEt2, OH) are highly sensitive and selective fluorescent probes for thiols in acidic solutions (pH 7) and promising dyes that can label lysosomes in live cells.
Dai, Chun-Guang,Du, Xiao-Jiao,Song, Qin-Hua
p. 12088 - 12099
(2016/01/09)

Design, synthesis and preliminary bioactivity evaluations of substituted quinoline hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors
Inhibition of HDACs activity has become a promising therapeutic strategy in clinical practice to reverse the abnormal epigenetic states of cancer and other diseases. Therefore, HDAC inhibitors become a relatively new class of anti-cancer agent. In the present study, we reported the design and synthesis of a series of novel HDAC inhibitors using various substituted quinoline rings as the cap group. In vitro studies showed that some compounds have good inhibitory activities against HDACs and potent antiproliferative activities in some tumor cell lines. Especially, compound 9w (IC50 = 85 nM), exhibited better inhibitory effect compared with SAHA (IC50 = 161 nM).
Wang, Lei,Hou, Xuben,Fu, Huansheng,Pan, Xiaole,Xu, Wenfang,Tang, Weiping,Fang, Hao
p. 4364 - 4374
(2015/08/03)

Strategically Modified Rhodamine-Quinoline Conjugate as a CHEF-Assisted FRET Probe for Au3+: DFT and Living Cell Imaging Studies
A systematic journey from O-donor through S-donor to N-donor chelator led to the development of a highly selective Au3+ chemosensor that operates via a CHEF-induced FRET mechanism. This sensing protocol avoids unwanted possible side reactions observed in alkyne-based gold sensors. DFT studies strongly support the experimental facts. The probe RT-2 detects Au3+ in the presence of the masking agent KI to minimize Hg2+ interference; however, RQ-2 selectively detects Au3+ without any interference and shows reversibility in the sensing in the presence of tetrabutylammonium cyanide. The probe efficiently images Au3+ in living HeLa cells under a fluorescence microscope.
Adhikari, Susanta,Mandal, Sandip,Ghosh, Avijit,Das, Pradip,Das, Debasis
p. 8530 - 8538
(2015/09/15)

Multiple dynamics of hydrazone based compounds
Hydrazone derivatives of 2-quinolinecarboxaldehyde and 6-bromo-2-pyridinecarboxaldehyde were synthesized by sequence reactions with hydrazine derivatives. These compounds exhibited E/Z isomerization upon irradiation using a mercury lamp (250 W). The configurational changes were monitored by 1H nuclear magnetic resonance (NMR), UV-Vis and fluorescence spectroscopy. Data of concentration of the E/Z isomers versus time showed first order kinetics with constants ranging from 0.024 to 0.0799 min-1. The Z isomers were isolated by chromatographic methods and characterized by 1H NMR, UV-Vis and fluorescence spectroscopy and X-ray diffraction. The Z compounds are stable even in solution for several months. Such stability is due to a thermodynamic stabilization by the formation of an intramolecular hydrogen bond in the Z structure, which is not seen in the E configuration. Furthermore, some of the compounds were used as ligands for various metal centers (Zn2+, Co2+ and Hg2+) and their electronic properties were studied including measurements of cyclic voltammetry. The compounds studied herein allow their use as dynamic systems in dynamic combinatorial chemistry as their properties can be modulated by light, heat and the presence of metal centers. Besides, obtaining a metastable state (Z-isomer) allows the use of these compounds as photo-brakes, and therefore they can be implemented as molecular machines.
Romero, Elkin L.,D'Vries, Richard F.,Zuluaga, Fabio,Chaur, Manuel N.
p. 1265 - 1273
(2015/06/16)

Synthesis, crystal structures, and fluorescent properties of zinc(II) complexes with benzazino-2-carboxalidin-2-aminophenols
Complexes ZnL2 with novel fluorinated benzazines as tridentate ligands (HL = 6,7-difluoroquinoxalinand 6,7-difluoroquinolincarboxalidin-2-aminophenol) have been prepared. The photophisical properties of the ligands and the complexes has been studied.
Nosova, Emiliya,Stupina, Tatyana,Chupakhin, Artem,Lipunova, Galina,Valova, Marina,Slepukhin, Pavel,Charushin, Valery
p. 61 - 67
(2016/10/13)

Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors
An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.
Zhang, Ying,Jiang, Xiao,Wang, Jin-Mei,Chen, Jing-Lei,Zhu, Yong-Ming
p. 17060 - 17063
(2015/03/30)

Iron-catalyzed C-H bond functionalization for the exclusive synthesis of pyrido[1,2-a]indoles or triarylmethanols
The efficient and selective iron-catalyzed C-H activation of 2-benzhydrylpyridine derivatives was employed for the preparation of pyrido[1,2-a]indoles through an intramolecular C-H amination reaction. In the presence of molecular oxygen as the sole oxidant, the same 2-benzhydrylpyridines were also used for the synthesis of the corresponding tertiary alcohols. In these approaches, the iron catalyst was used to selectively activate the C(sp2)-H bond of 2-benzhydrylpyridine, in the case of the intramolecular ring-closing C-H amination reaction in which the pyridine nitrogen atom was a directing group as well as a nucleophile, and the C(sp3)-H bond of the same compound, in the case of the oxidation reaction to give the corresponding triaryl carbinol.
Karthikeyan, Iyyanar,Sekar, Govindasamy
supporting information
p. 8055 - 8063
(2015/01/09)