- 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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supporting information
p. 5049 - 5055
(2021/07/29)
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- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
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Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
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p. 5599 - 5604
(2021/08/01)
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- Compound as potassium channel modulator
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The invention relates to a compound as a potassium channel modulator, which is a compound of a formula (I) or a pharmaceutically acceptable salt thereof. The compound or the pharmaceutically acceptable salt thereof is effective for curing and preventing diseases and symptoms influenced by the activity of potassium ion channels.
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Paragraph 0486; 0488; 0491; 0492
(2018/07/30)
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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 0073; 0074
(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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- Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines
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A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.
- Zaugg, Cornelia,Schmidt, Gunther,Abele, Stefan
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p. 1003 - 1011
(2017/07/26)
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- Tetrahydroquinoline analogues as muscarinic agonists
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The present invention relates to tetrahydroquinoline compounds as muscarinic receptor agonists; compositions comprising the same; methods of inhibiting an activity of a muscarinic receptor with said compounds; methods of treating a disease condition associated with a muscarinic receptor using said compounds; and methods for identifying a subject suitable for treatment using said compounds.
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Page/Page column 34
(2017/01/05)
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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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- ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND METHOD OF USING THEREOF
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The present invention relates to novel anthelmintic compounds of formula (I) below: wherein Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X1, X2, X3, X4, X5, X6, X7 and X8 are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.
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Paragraph 0446; 0447
(2014/05/25)
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- NITROGEN HETEROCYCLIC COMPOUNDS USEFUL AS PDE10 INHIBITORS
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Unsaturated nitrogen heterocyclic compounds of formula (I): (I), as defined in the specification, compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, Huntington's Disease, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
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Page/Page column 183
(2011/12/02)
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- Identification and specificity studies of small-molecule ligands for SH3 protein domains
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The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with Kd = 125 μM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2- aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.
- Inglis, Steven R.,Stojkoski, Cvetan,Branson, Kim M.,Cawthray, Jacquie F.,Fritz, Daniel,Wiadrowski, Emma,Pyke, Simon M.,Booker, Grant W.
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p. 5405 - 5417
(2007/10/03)
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- ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS
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Compounds of the formula I: are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive-compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.
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- Pesticides
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Compound of the formula (I) are disclosed or a salt thereof, wherein Ar is an optionally substituted polycyclic ring system containing n rings, where n is the integer 2 or 3, at least n-1 rings being aromatic and containing one to three ring nitrogen atoms and optionally containing one or more additional heteroatoms; Q is an alkyl chain containing 1 to 12 carbon atoms and optionally containing a sulphur or one or two oxygen atoms; Q1 is a group (C(R2)=C(R3))a --(C(R4)=C(R5)) wherein a is 0 or 1, R2, R3, R4 and R5 are the same or different, at least two being hydrogen and the other two being independently selected from hydrogen, halo, C1-4 haloalkyl; X is oxygen or sulphur; and R1 is selected from hydrogen and C1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C1-6 alkoxy are described which have activity particularly against arthropod pests. Pesticidal formulations containing the compounds of the formula (1), their use in the control of pests and method for their preparation are also disclosed.
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