- 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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- Enantioselective Synthesis of Diaryl Sulfoxides Enabled by Molecular Recognition
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The enantioselective sulfoxidation of diaryl-type sulfides was accomplished using a chiral manganese porphyrin complex equipped with a remote molecular recognition site. Despite the marginal size difference between the two substituents at the prostereogen
- Burg, Finn,Buchelt, Christoph,Kreienborg, Nora M.,Merten, Christian,Bach, Thorsten
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supporting information
p. 1829 - 1834
(2021/03/08)
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- Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions
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An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.
- Annapureddy, Rajasekar Reddy,Burg, Finn,Gramüller, Johannes,Golub, Tino P.,Merten, Christian,Huber, Stefan M.,Bach, Thorsten
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supporting information
p. 7920 - 7926
(2021/03/03)
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- CRBN LIGANDS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
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Paragraph 00557; 00560; 00561
(2019/08/20)
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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 0035; 0036; 0037; 0038
(2018/12/05)
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- Palladium-catalyzed synthesis of quinolin-2(1: H)-ones: the unexpected reactivity of azodicarboxylate
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Quinolin-2(1H)-one is a useful structure unit present in a wide range of natural products and pharmaceuticals. A Pd(ii)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides was developed with azodicarboxylates which act as both the activating agent and oxidant. The reaction proceeded under mild conditions and no protection against air and moisture was needed.
- Peng, Jin-Bao,Chen, Bo,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 1632 - 1635
(2018/03/21)
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- 2,4-DIOXO-QUINAZOLINE-6-SULFONAMIDE DERIVATIVES AS INHIBITORS OF PARG
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The present invention relates to compounds of formula I that function as inhibitors of PARG (Poly ADP-ribose glycohydrolase) enzyme activity wherein R1a, R1b, R1c, R1d, R1e, W, X1, X2, X3, X4, X5, X6, X7, c are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which PARG activity is implicated.
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Page/Page column 104; 257
(2016/07/05)
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- A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions
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The indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3), and isoneocryptolepine (4) are important tools in traditional medicine. Now, their precursors 1a-4a were synthesized in two steps starting from the corresponding bromo-iodoquinolines. Our strategy is based on palladium-catalyzed reactions, applying regioselective Buchwald-Hartwig amination on 2,3- and 3,4-dihaloquinolines followed by an intramolecular Heck-type reaction. Both steps were carried out under microwave irradiation.
- Bogányi, Borbála,Kámán, Judit
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p. 9512 - 9519
(2013/10/08)
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- NOVEL NITROGENATED HETEROCYCLIC COMPOUND AND SALT THEREOF
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A nitrogen-containing heterocyclic compound represented by the general formula: wherein the dashed line represents a single bond or a double bond; R1, R2, R3, R4 and R5 independently represent a hydrogen atom, halogen atom, a lower alkyl, aryl, lower alkoxy or monocyclic heterocyclic group which may be substituted or the like; R6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted; X1 represents a lower alkylene group or the like; X2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted; X3 represents an oxygen atom, sulfur atom, a sulfinyl group, sulfonyl group or the like; Y1 represents a bivalent cyclic group, containing a nitrogen, which may be substituted or the like; and Z1 represents a nitrogen atom, a carbon atom which may be substituted or the like, or a salt thereof. The compound or salt has a potent antibacterial activity and a high safety, and is therefore useful as an excellent antibacterial agent.
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Page/Page column 108
(2010/11/30)
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- A concise synthesis of a novel antiangiogenic tyrosine kinase inhibitor
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(Chemical Equation Presented). An efficient synthesis of the potent KDR inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indole-2-yl] quinolin-2(1H)-one (1) is described. The process features a noncryogenic indole boronation and a dicyclohexylamine-mediated Suzuki coupling.
- Payack, Joseph F.,Vazquez, Enrique,Matty, Louis,Kress, Michael H.,McNamara, James
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p. 175 - 178
(2007/10/03)
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- A novel and efficient synthesis of 2,3-dichloroquinoline
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2,3-Dichloroquinoline was prepared in three steps in good overall yield from commercial 3-bromoquinoline via N-oxide formation and rearrangement to 3-bromocarbostyril, followed by a one-pot conversion to 3-bromo-2- chloroquinoline and halogen exchange to the title compound.
- Sabol, Mark R.,Owen, John M.,Erickson, W. Randal
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p. 427 - 432
(2007/10/03)
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- A Convenient Synthesis of Two New Indoloquinoline Alkaloids
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A concise synthesis of two new indoloquinoline-based alkaloids (1 and 2), isolated from Cryptolepis sanguinolenta, is reported. The palladium-catalyzed cross-coupling reaction of 3-bromoquinoline derivatives with N-pivaloylamino phenylboronic acid gave th
- Timári, Géza,Soós, Tibor,Hajós, Gy?rgy
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p. 1067 - 1068
(2007/10/03)
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- Metallation of 2(1H)-quinolinone: Synthesis of 3-substituted compounds
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The ortho-directing effect of the amide function in the regioselective lithiation of 2(1H)-quinolinone has been confirmed. Direct or indirect electrophilic substitution may compete with previous multistep procedures to obtain 3-substituted compounds.
- Fernandez,De La Cuesta,Avendano
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p. 1362 - 1364
(2007/10/02)
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- REACTIONS OF 3-SUBSTITUTED QUINOLINE 1-OXIDES WITH ACYLATING AGENTS
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Reactions of 3-fluoro- (1a), 3-bromo- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table).While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxyquinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.
- Miura, Yutaka,Takaku, Sakae,Nawata, Yoshiharu,Hamana, Masatomo
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p. 1579 - 1586
(2007/10/02)
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- Methyl substituted imidazol-1-yl quinolones
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A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared wherein the heterocyclic ring moiety is a substituted pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the
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