- A facile synthesis of novel 9-methyl[1,2,3]selenadiazoles[4,5-b]quinoline and 9-methyl[1,2,3]thiadiazole[4,5-b]quinoline as a new class of antimicrobial agents
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2-chloro-4-methyl quinoline 2 on condensation with semicarbazide hydrochloride gave its semicarbazone. This on reaction with SeO2 and SOCl2 yielded a new class of novel selenadiazoles 4 and thiadiazoles 5, respectively. The structure of all the compounds were elucidated on the basis of elemental analysis, IR, 1H NMR, and the mass spectral data. Some derivatives of 9-methyl[1,2,3]selenadiazole[4,5-b] quinoline and 9-methyl[1,2,3]thiadiazole [4,5-b]quinoline have been screened for antimicrobial activities. Copyright Taylor & Francis Group, LLC.
- Bhojya Naik, Halehatty S.,Ramesha, Machenahalli S.,Swetha, Boovanahalli V.,Roopa, Thopenahalli R.
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- Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
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Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
- Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
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supporting information
p. 23193 - 23196
(2021/09/25)
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- Computational and Synthetic approach with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S triple mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)
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New substituted quinoline derivatives were designed and synthesized via a five-step modified Suzuki coupling reaction. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. All docking studies confirmed high potency and flexibility towards wild type as well as a mutated enzyme. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M/C797S and L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Most of the quinoline derivatives revealed a significant cytotoxic effect. The IC50 values of 4-(4-methylquinolin-2-yl)phenyl 4-(chloromethyl)benzoate (5j) were found to be 0.0042 μM, 0.02 μM, 1.91 μM, 3.82 μM and 3.67 μM while IC50 values of osimertinib were 0.0040 μM, 0.02 μM, ND, 0.99 μM and 1.22 μM, respectively. Compound 5j has shown excellent inhibitory activities against EGFR kinases triple mutant with IC 50 value 1.91 μM. It was observed that, compared to H1975, A549 and A431 cell lines, synthesized compounds significantly inhibited proliferation of the HCC827 cell line. These data suggested that synthesized compounds showed promising selective anticancer activity against tumor cells harboring EGFR Del E746-A750. The potency of compound 5j was compared through molecular dynamic simulations and an insilico ADMET study. QSAR models were generated and the best model was correctly compared with respect to predicted and observed activity of compounds. The built model will assist to design, refine and construct novel substituted quinoline derivatives as potent EGFR inhibitors in near future.
- Karnik, Kshipra S.,Sarkate, Aniket P.,Tiwari, Shailee V.,Azad, Rajaram,Burra, Prasad V.L.S.,Wakte, Pravin S.
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- Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)
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Two different schemes of novel substituted quinoline derivatives were designed and synthesized via simple reaction steps and conditions. A comparative molecular docking study was carried out on two different types of EGFR enzymes which include wild-type (PDB: 4I23) and T790M mutated (PDB: 2JIV) respectively. Compounds were also validated upon T790M/C797S mutated (PDB ID: 5D41) EGFR enzyme at the allosteric binding site. Free energy perturbations were carried out to determine the absolute binding free energy of a protein–ligand complex in the form of ΔGbinding, which in turn provided 4ab and 5ad as the most potential contenders through the structural enhancement in the determined initial scaffolds. Anticancer activity of the synthesized derivatives was examined against HCC827, H1975 (L858R/T790M), A549, and HT-29 cell lines by standard MTT assay. Compound 4ad (6-chloro-2-(isoindolin-2-yl)-4-methylquinoline) has shown excellent inhibitory activities against mutant EGFR kinase with IC50 value 0.91 μM. The potency of compounds 4ab, 4ad and 5ad was compared through an insilico ADMET study.
- Azad, Rajaram,Karnik, Kshipra S.,Sarkate, Aniket P.,Tiwari, Shailee V.,Wakte, Pravin S.
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- Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents
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A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.
- Nan, Jiang,Chen, Pu,Gong, Xue,Hu, Yan,Ma, Qiong,Wang, Bo,Ma, Yangmin
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supporting information
p. 3761 - 3766
(2021/05/10)
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- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
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A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
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supporting information
p. 2095 - 2103
(2021/03/26)
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- Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
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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
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p. 5049 - 5055
(2021/07/29)
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- HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst
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A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
- Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.
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supporting information
(2020/10/20)
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- Lactamization of alkenyl C-H bonds to generate 2-quinolinones with triphosgene
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A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.
- Du, Guizhi,Wang, Zixiao,Zhang, Zhen
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p. 600 - 608
(2020/06/03)
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- Synthesis and antileishmanial evaluation of thiazole orange analogs
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Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.
- Abdelhameed, Ahmed,Liao, Xiaoping,McElroy, Craig A.,Joice, April C.,Rakotondraibe, Liva,Li, Junan,Slebodnick, Carla,Guo, Pu,Wilson, W. David,Werbovetz, Karl A.
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supporting information
(2019/11/28)
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- Discovery, synthesis and molecular substantiation of N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides as anticancer agents
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The effort was taken to develop a series of benzothiazole and quinoline fused bioactive compounds obtained through a four-step synthetic route using a range of substituted acetoacetanilides. Achieved N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides (6a-l) were produced up to 96% of yield while the eco-friendly p-TSA used as a catalyst. Further, the anticancer activity of these compounds was determined using a range of cancer cell lines starting from MCF-7 (Breast cancer), HCT-116 (Colon cancer), PC-3 & LNCaP (Prostate) and SK-HEP-1 (Liver cancer). Present study compounds were also testified for antioxidant properties prior to anticancer studies since the Reactive Oxygen Species (ROS) being vital in cancer development. To determine the cell membrane stability effects of the compounds, human red blood cells (HRBC) based membrane protection assay was determined. In the results, compounds 6a-l were able to produce a dominated result values over PC3 cell lines (Prostate cancer) than the other cell lines used in this study. Since the connectivity of human germ cell alkaline phosphatase (hGC-ALP) in the development of prostate cancer is known, the most active compounds were evaluated for the hGC-ALP inhibition in order to ensure a mechanism of anticancer action of these compounds. The mode of interaction and binding affinity of these compounds was also investigated by a molecular docking study. In the results, 6d, 6i, 6k, and 6l were found with least IC50 values 0.075 μM and highest relative activity of 92%, 90%, and 96% respectively. The need for further animal model evaluation and pre-clinical studies recognized.
- Bindu,Vijayalakshmi,Manikandan
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- A cascade approach to 3D cyclic carbamates: Via an ionic decarboxylative functionalization of olefinic oxamic acids
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An m-CPBA-mediated intramolecular epoxidation-decarboxylative alkoxylation cascade reaction of olefinic oxamic acids has been developed. The distinct ionic decarboxylative mechanism was preliminarily revealed. The protocol features mild reaction conditions and operational simplicity, allowing the construction of diverse medicinally valuable 5-7 membered 3D cyclic carbamate architectures in moderate to high yields.
- Fan, Huaqiang,Wan, Yi,Pan, Peng,Cai, Wenbin,Liu, Shihui,Liu, Chuanxu,Zhang, Yongqiang
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- Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline
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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.
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p. 891 - 901
(2018/09/25)
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- Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature
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A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.
- Fan, Huaqiang,Pan, Peng,Zhang, Yongqiang,Wang, Wei
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p. 7929 - 7932
(2019/01/04)
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- 2 - (1 H) - quinoline compound of microwave-assisted synthesis method (by machine translation)
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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 0065; 0066
(2018/09/28)
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- Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions
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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
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supporting information
p. 760 - 764
(2018/02/14)
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- Preparation method of 2-quinolinone compounds
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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 0039; 0040; 0041
(2018/12/05)
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- A nitrogen oxide C2 - bit hydroxylated method (by machine translation)
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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; 0036-0038; 0045-0050
(2017/05/19)
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- IMDAF Cascade Approach toward the Synthesis of the Alkaloid (±)-Minfiensine
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The total synthesis of the Strychnos alkaloid (±)-minfiensine was achieved via an intramolecular amidofuran Diels-Alder cycloaddition/rearrangement followed by an iminium ion/cyclization cascade sequence. This domino process provides for a rapid access to the unique 1,2,3,4-tetrahydro-9a,4a-iminoethanocarbazole core structure found in the alkaloid minfiensine (2). In this paper, the full account of our synthetic study is described, highlighting the successful application of the cascade sequence to form the A/B/C/D rings of (±)-minfiensine (2) in high yield. A palladium-catalyzed enolate coupling reaction was then used to furnish the final E ring and complete the total synthesis of (±)-minfiensine (2).
- Leverett, Carolyn A.,Li, Gang,France, Stefan,Padwa, Albert
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p. 10193 - 10203
(2016/11/17)
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- Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral
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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
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supporting information
p. 7068 - 7072
(2016/07/06)
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- Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
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The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).
- Xia, Shanghua,Gan, Lu,Wang, Kailiang,Li, Zheng,Ma, Dawei
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supporting information
p. 13493 - 13496
(2016/10/31)
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- Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
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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
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supporting information
p. 222 - 225
(2015/01/30)
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- Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones
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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
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supporting information
p. 3568 - 3571
(2014/07/21)
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- Synthesis of 2(1 H)-quinolinones via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylanilines
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Palladium-catalyzed oxidative cyclocarbonylation of N-monosubstituted-2- vinylanilines constitutes a simple, direct, and selective method for the synthesis of 2(1H)-quinolinones. The reaction conditions are attractive in terms of environmental considerations and operational simplicity. 2(1H)-Quinolinones with a variety of functional groups were prepared in up to 97% yield.
- Ferguson, Jamie,Zeng, Fanlong,Alwis, Natacha,Alper, Howard
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supporting information
p. 1998 - 2001
(2013/06/04)
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- C-O cross-coupling of activated aryl and heteroaryl halides with aliphatic alcohols
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A robust and general catalyst system facilitates the alkoxylation of activated heteroaryl halides with primary, secondary, and select tertiary alcohols without the need for an excess of either coupling partner (see scheme). This catalyst system displays broad functional-group tolerance and excellent regioselectivity, and is insensitive to the order of reagent addition. Copyright
- Maligres, Peter E.,Li, Jing,Krska, Shane W.,Schreier, John D.,Raheem, Izzat T.
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supporting information
p. 9071 - 9074
(2012/10/30)
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- An environmentally benign one pot synthesis of substituted quinolines catalysed by fluoroboric acid based ionic liquid
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Organic synthesis generally required large amount of solvent, avoiding the use of organic solvents in synthesis is a paradigm shift directed at developing more benign chemistry, and with ionic liquids surprisingly can lead to access to new compounds. An elegant one-pot synthesis of quinoline derivatives has been achieved by reaction of substituted anilines with β-ketoester at 60°C in ethanol using an ionic liquid [Et3NH]+[BF 4]- as catalyst. All the reactions gave products with high degree of purity and excellent yield (78.93%) within the shorter span of time (20.65 min) than those reactions with conventional methods. The screening of solvents as well as the reuse of ionic liquid has been evaluated. The structure of the products has been elucidated by spectral and analytical data. The present scope and potential economic impact of the reaction are demonstrated by the synthesis of substituted quinolines. Remaining challenges and future perspectives of the new transformation are discussed.
- Rajendran, A.,Karthikeyan, C.,Rajathi, K.,Ragupathy, D.
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p. 877 - 881,5
(2020/09/09)
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- Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
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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
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p. 5803 - 5809
(2012/11/07)
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- Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities
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An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
- Maiti, Arup,Reddy, P. V. Narasimha,Sturdy, Megan,Marler, Laura,Pegan, Scott D.,Mesecar, Andrew D.,Pezzuto, John M.,Cushman, Mark
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experimental part
p. 1873 - 1884
(2009/12/31)
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- An environmentally benign indium (III) chloride catalysed one-pot synthesis of quinolines
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A convenient eco-friendly procedure for the quantitative synthesis of novel quinoline derivatives has been developed by a simple one-pot reaction of substituted anilines with P-ketoesters at 60°C in ethanol using recyclable indium chloride as catalyst. The reaction proceeds smoothly under solvent free conditions with quantitative yields.
- Kidwai, Mazaahir,Bansal, Vikas,Mishra, Neeraj Kumar,Bhatnagar, Divya
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experimental part
p. 746 - 748
(2009/12/28)
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- A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis
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A general synthesis of quinolinones and benzothiazine 1,1-dioxides is presented. A series of N-phenylacrylamides and N-phenylethylenesulfonamides were studied for their ability to undergo ring closing methathesis to yield the corresponding quinolinones and benzothiazine 1,1-dioxides, respectively. The reactions are general in scope and represents a mild method for the preparation of these heterocycles.
- Minville, Joannie,Poulin, Jason,Dufresne, Claude,Sturino, Claudio F.
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p. 3677 - 3681
(2008/09/20)
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- Microwave-assisted solvent-free synthesis of 4-methyl-2-hydroxy- And 2-methyl-4-hydroxyquinolines
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Rapid and efficient microwave-assisted synthesis of 4-methyl-2-hydroxy- and 2-methyl-4-hydroxyquinolines from anilines and ethyl acetoacetate under different conditions is described.
- Nadaraj,Selvi, S. Thamarai
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p. 1203 - 1207
(2008/09/18)
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- Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions
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The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that. N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by β-elimination of the tosyl radical.
- Benati, Luisa,Bencivenni, Giorgio,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
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p. 3192 - 3197
(2007/10/03)
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- Intramolecular Wittig reactions. A new synthesis of coumarins and 2-quinolones
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o-Hydroxybenzaldehydes (1a-d) on reaction with chloroacetyl chloride in presence of pyridine followed by addition of triphenyl phosphine and base gave coumarins (2a-d). A similar sequence of reactions on o-aminoacetophenone/benzophenone (1e-f) and methyl anthranilate (1g) gave the corresponding 2-quinolones (2e-g).
- Desai, Vidya G.,Shet, Jyoti B.,Tilve, Santosh G.,Mali, Raghao S.
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p. 628 - 629
(2007/10/03)
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- The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes
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A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.
- Kobayashi, Kazuhiro,Kitamura, Taichi,Yoneda, Keiichi,Morikawa, Osamu,Konishi, Hisatoshi
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p. 798 - 799
(2007/10/03)
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- Carbamoyl radicals from se-phenylselenocarbamates: Intramolecular additions to alkenes
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A series of 5 exo-trig cyclizations of carbamoyl radicals generated from readily available Se-phenylselenocarbamates is reported. Kinetic studies indicate that the rate constant of this cyclization exceeds 1 x t 08s-1 in several cases.
- Rigby, James H.,Danca, Diana M.,Horner, John H.
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p. 8413 - 8416
(2007/10/03)
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- Synthesis of 7-Methyl-1,2-dihydroquinolin-2-ones as Angiotensin II Receptor Antagonists
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A number of biphenyl substituted 1,2-dihydroquinolin-2-ones were synthesized by regiospecific alkylation of the corresponding 1H-derivatives.Again, these precursors were prepared in three steps by acetoacetylation of anilines, regiospecific C-alkylation of the resulting β-ketoanilides and subsequent condensation to the quinolines.One of the target compounds, 2--1,2-dihydroquinolin-3-yl>-N,N-dimethylacetamide (10e), is a potent angiotensin II receptor antagonist.
- Beier, Norbert,Labitzke, Erwin,Mederski, Werner W.K.R.,Radunz, Hans-Eckart,Rauschenbach-Ruess, Karin,Schneider, Bjoern
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p. 117 - 132
(2007/10/02)
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- Studies on Cyclization of Allylacetoacetanilides and Spectral Characterisation of the Products
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Ring-closure of some α-(γ-substituted-allyl)acetoacetanilides has been studied.Ir and pmr spectra have been used to distinguish between the furoquinolines and pyranoquinolines obtained.Pmr spectra of some 2-substituted 2,3-dihydro-4-methylfuroquinolines (2) and 2-substituted 3,4-dihydro-5-methyl-2H-pyranoquinolines (4) are reported.The dihydropyranoquinolines are found to have three characteristic ir absorptions of diagnostic value.Orthophosphoric acid (OPA) appears to be superior to the widely used PPA or sulphuric acid as the cyclising agent for acetoacetanilides.
- Ashrof, M. A.,Raman, P. S.
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p. 733 - 738
(2007/10/03)
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- OXYGENATION OF THE UNACTIVATED PYRIDINE SYSTEM BY ACETYL HYPOFLUORITE MADE DIRECTLY FROM F2
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Acetyl hypofluorite was found capable of activating the usually unreactive pyridine by substituting the hydrogen at the 2 position by an acetoxy group which then was hydrolyzed to the corresponding pyridinone.Substitutents at 3, 4 or 5 position do not interfere with the reaction, but compounds with substituents at 2 (with the exception of aromatic ones) either do not react or produce tars.The reaction conditions are very mild and the yields are very good for this kind of substitution.Quinolines and pyrazines also react very satisfactorily.
- Rozen, Shlomo,Hebel, David
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p. 249 - 258
(2007/10/02)
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- Polycyclic N-Hetero Compounds. XXIV. Reaction of Pyridine and Quinoline N-Oxides with N-Methylformamide
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Reactions of pyridine and quinoline N-oxides with N-methylformamide are described.N-Methylcarbamoylation occured at the C-2 or C-4 position of pyridine and quinoline derivatives.Keywords - pyridine N-oxide; quinoline N-oxide; N-methylformamide; N-methylcarbamoylation; N-oxide; formamide; carbamoylation
- Hirota, Takashi,Namba, Tetsuto,Sasaki, Kenji
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p. 3431 - 3434
(2007/10/02)
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- RING CLEAVAGE AND RING EXPANSION OF INDOLES BY SUPEROXYDE ION
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The reaction of indoles (1) with superoxide ion resulted in ring cleavage to give o-formyl and o-acylaminoketones (6) or N-acylanthranilic acid (8) and ring expansion yielding 2-quinolones (7).All reactions are chemiluminescent except that of 2-methylindole (1h), which gave a coupled product (9).
- Balogh-Hergovich, E.,Speier, G.
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p. 4473 - 4476
(2007/10/02)
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