- Palladium-Catalyzed Synthesis of 1 H -Pyrazolo[4,3- c ]quinolines and 4-Anilinoquinoline-3-carbonitriles from 4-Chloroquinoline-3-carbaldehydes
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Novel 1H-pyrazolo[4,3-c]quinolines and 4-anilinoquinoline-3-carbonitriles were prepared from readily accessible 4-chloroquinoline-3-carbaldehyde hydrazones by palladium-catalyzed intramolecular C-N bond formation and concurrent hydrazine N-N bond fission. These two classes of functionalized quinolines were chromatographically separable, and both are of biological interest. The ratio of the two products was found to be temperature-dependent; by changing the reaction temperature, either the pyrazoloquinoline or the anilinoquinolinecarbonitrile can become the dominant product.
- Wang, Chao,Tang, Caifei,Li, Zhiming,Wang, Quanrui
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- 2H-Pyrano[3,2-c]quinolin-2-ones: their convenient synthesis and selected reactions
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Abstract: Despite the structure attractiveness of 2H-pyrano[3,2-c]quinolin-2-ones 3 their synthesis is not sufficiently developed. Only 35 pyranoquinolinones 3 are registered in the SciFinder database. Unavailability of 3 limits their chemistry exploitation, physical and biological studies. We have developed a convenient and general methodology for the synthesis of 3. Sixteen novel 2H-pyrano[3,2-c]quinolin-2-ones 3 were prepared by a cyclocondensation of easily available 4-oxo-1,4-dihydroquinoline-3-carbaldehydes 1 with monosubstituted acetic acids 2 (-aryl, -arylthio and -heteroaryl). To support chemistry exploitation of pyranoquinolinones 3, oxoquinolinylphenylacrylic acids 4 were obtained by hydrolysis of 3 with NaOH (92–98%). A simple oxidation of 3 by MCPBA was performed to provide oxopyranoquinoline N-oxide 5 (71%). Convenient rearrangement of 5 in refluxing Ac2O curried out 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione 6 in 87% yield. Moreover, some of the prepared pyranoquinolinones 3 possess intensive blue fluorescence properties. Here we described the simple and general synthesis that allows availability of 2H-pyrano[3,2-c]quinolin-2-ones 3. Some transformations of 3 to the novel heterocyclic compounds 4–6 were performed as well in good yields (71–98%). The synthesis of 6 from 3 was not yet described. The developed methodology for the synthesis of 3–6 can stimulate their further physical and pharmacological studies. Graphical Abstract: [Figure not available: see fulltext.].
- ?akurda, Matú?,Koi?, Pavol,Addová, Gabriela,Lácová, Margita,Bohá?, Andrej
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- HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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Page/Page column 53-54
(2021/06/22)
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- FUNCTIONALIZED HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compound-linker constructs and antibody-drug-conjugates of compounds of formula (I) that are useful as modulators of STING (Stimulator of Interferon Genes).
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Page/Page column 89
(2021/06/22)
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- Quinolinone compound and application thereof
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The invention discloses a quinolinone compound containing rhodanine and similar fragments thereof and pharmaceutically acceptable salts thereof, and relates to the technical field of organic chemistry. The quinolinone compound is shown as general formula I in the specification, wherein substituent groups R1, X and R2 have meanings given in the specification. The invention also relates to application of the compound shown as the general formula I and the pharmaceutically acceptable salts thereof in preparing medicines for treating diseases caused by abnormal expression of IDO, in particular toapplication in preparing medicines for treating and/or preventing cancers.
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Paragraph 0055-0056; 0058-0059
(2020/07/12)
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- NEXT-GENERATION MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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Page/Page column 74-75
(2020/12/30)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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- Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[: D] thiazol-2-ylimino)butyl)-4 H -chromen-4-one
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Using 2-propanol as the solvent, 3-formylchromones and 2-aminobenzothiaoles formed corresponding imines, while 1° and 2°-alcohols formed the corresponding 2-alkoxy-3-enamines with selectivity for the Z-isomer. Changing the substrates with similar molecules such as 3-formylchromone with quinoline-, quinolone- and indole-3-carbaldehydes sometimes resulted in the formation of the corresponding imines, whereas replacing 2-aminobenzothiazole with amides resulted in the formation of acetals. Considering the effect of the solvent, replacing alcohols with the aprotic solvents THF and CH2Cl2 resulted in the formation of imines and enamines, which are the characteristic reactions of 2-propanol and other 1° and 2°-alcohols, respectively. 2-Alkoxy-3-enamines were found to undergo transacetalization with both short and long chain alcohols. The novelty of these reactions is that they did not require an external catalyst, all the reactions were performed at the same temperature, and purification was achieved by filtration. The transacetalization we performed herein is a new concept, which has not been reported to date. In contrast, other similar reactions, such as transalkoxylation, transalkylation, and transetherification, are performed on a commercial scale using expensive catalysts such as Otera's catalyst. The highly sensitive nature of 3-formylchromones towards variations in the substrates and solvents to form different products and the reason behind the selective formation of the Z-isomer of 2-alkoxy-3-enamines and its transacetalization efficiency need further studies to understand the reaction mechanism and possibly other factors such as solvent effects.
- Ahmed, Owais,Cherkadu, Vandana,Kalavagunta, Praveen Kumar,Shang, Jing
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p. 20573 - 20581
(2019/07/12)
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- Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1 H)-ones under Irradiation with 365 nm UV Light
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A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of (E)-3-styrylquinolin-4(1 H)-ones in EtOH-H 2 O (7:1) with UV light (365 nm) at room temperature under Ar atmosphere. The demonstrated photoinduced intramolecular rearrangement has advantages over other transition-metal-catalyzed reactions, e.g. no requirement of additives, green solvent, broad substrate scope, and high atom efficiency.
- Jing, Sisi,He, Yun,Wang, Tao,Zhang, Jin,Cheng, Anqi,Liang, Yong,Zhang, Zunting
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supporting information
p. 1578 - 1582
(2018/06/26)
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- Continuous-flow preparation and use of β-chloro enals using the Vilsmeier reagent
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The Vilsmeier reagent is used in the preparation of a wide variety of heterocycles, such as pyrazoles, via formation of β-chloroacrolein intermediates. However, use of this extremely reactive reagent on large scale requires special precautions to avoid potentially dangerous exotherms. This article describes the safe preparation at room temperature of the Vilsmeier reagent under flow conditions for the formation of β-chloroacroleins and 3-formylchromones, as well as the use of these in multistep, continuous flow processes for the syntheses of β-acrylonitriles and polysubstituted pyrazoles.
- Pellegatti, Laurent,Buchwald, Stephen L.
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supporting information
p. 1442 - 1448
(2012/10/29)
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- An experimental NMR and computational study of 4-quinolones and related compounds
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We report the synthesis and structural study of eight compounds, either quinolin-4(1H)-ones or quinolines. Tautomerism as well as (E) → (Z) and rotational isomerism were studied both experimentally (1H and 13C NMR) and theoretically [B3LYP/6-311++G(d,p)]. Springer-Verlag 2011.
- Seixas, Raquel S.G.R.,Silva, Artur M.S.,Alkorta, Ibon,Elguero, Jose
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experimental part
p. 731 - 742
(2012/06/29)
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- 3-Hydroxypyrrolo[2,3-b]pyridine and related compounds - Indoxyl analogues with fused electron deficient rings
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Flash vacuum pyrolysis (FVP) of 4-acetyltetrazolo[1,5-a]pyridine 5 at 400 °C provides 3-methyl isoxazolo[3,4-b]pyridine 6 whose structure was confirmed by X-ray crystallography. At higher pyrolysis temperatures, the unstable heteroindoxyl 8 was obtained, which exists as the keto form (1,2-dihydropyrrolo[2,3-b]pyridin-3-one) 8K in CDCl3 solution and the enol tautomer (3-hydroxypyrrolo[2,3-b]pyridine) 8E in DMSO. The heteroindoxyl 8 oxidatively dimerises to the heteroindigotin 9, undergoes condensation reactions at the 2-position and reacts with methoxymethylene Meldrum's acid at the 1-position. FVP of the corresponding acetyltetrazolo[1,5-a]quinoline 19 was much more complex, with 2-(cyanophenyl)acetonitrile 30 (rather than a heteroindoxyl) the major product at 750 °C. FVP of 3-acetyl-4-azidoquinoline 24 at 400 °C gave 3-methylisoxazolo[4,3-c]quinoline 33, but rearrangement to the heteroindoxyl was not observed at higher temperatures.
- Gaywood, Alexander P.,McNab, Hamish
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supporting information; experimental part
p. 5166 - 5173
(2010/12/25)
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- METHYL SULFANYL PYRMIDMES USEFUL AS ANTIINFLAMMATORIES, ANALGESICS, AND ANTIEPILEPTICS
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The present invention relates to pyrimidine derivatives of Formula (Ia) and (Ib) (including tautomers, isomers, prodrugs, and pharmaceutically acceptable salts thereof). Said compounds are useful in the treatment of pain (such as neuropathic pain), inflammation, and epilepsy (by acting as anticonvulsants). Methods of medical treatment making use of said compounds, as well as additional compounds of Formula (IIa) and (IIb), are also disclosed.
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Page/Page column 94
(2010/12/18)
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- Efficient consecutive alkylation-Knoevenagel functionalisations in formyl aza-heterocycles using supported organic bases
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An efficient solution-phase parallel procedure to perform the structural diversification of some formyl aza-heterocycles employing supported organic bases (PS-BEMP, PS-TBD or Si-TBD) is described. The library synthesis is based on a consecutive alkylation-Knoevenagel functionalisation that employs alkyl halides, Michael acceptors, and malonic acid derivatives as diversity elements. Georg Thieme Verlag Stuttgart.
- Coelho, Alberto,El-Maatougui, Abdelaziz,Ravi?a, Enrique,Cavaleiro, José A. S.,Silva, Artur M. S.
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p. 3324 - 3328
(2008/09/17)
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- A novel one-pot synthesis of 4-chloro-3-quinolinecarboxaldehydes, 4-chloroquinolines and 4-chloro-3-ethylquinolines using Vilsmeier reagent
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Various substituted l-(2-aminophenyl)ethanones on treatment with Vilsmeier reagent at 90°C for 3-6 hr yield 4-chloro-3-quinolinecarboxaldehydes. Whereas substituted N-[2-(1- oxoethyl) phenyl] acetamides afford both 4-chloroqui-nolines and 4-chloro-3-quinolinecarboxaldehydes. However, in the case of substituted l-(2-aminophenyl)butanones and N-[2(1-oxopropyl) phenyl] acetamides, only 4-chloro-3-ethylquinolines are obtained.
- Amaresh,Perumal
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p. 541 - 544
(2007/10/03)
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