- Regiodivergent Visible Light-Induced C–H Functionalization of Quinolines at C-5 and C-8 under Metal-, Photosensitizer- and Oxidant-Free Conditions
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A general strategy towards the selective perfluoroalkylation of quinoline derivatives at C-5 and C-8 is described. This exceptionally mild radical transformation, compatible with a large panel of substrates, does not require any transition metal catalysts or oxidants. Outstandingly, visible light photoinduction using simple household bulbs, in the absence of a photosensitizer, is the unique activation mode. Further importance of this reaction relies on its capacity to functionalize selectively both C-5 and C-8 positions of quinolines. This transformation, perfectly fulfilling green chemistry requirements, allows a truly practical and straightforward access to a variety of unprecedented functionalized amino- and amidoquinoline skeletons, presenting attractive features for medicinal and agrochemical industry. (Figure presented.).
- Arockiam, Percia Beatrice,Guillemard, Lucas,Wencel-Delord, Joanna
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supporting information
p. 2571 - 2579
(2017/08/16)
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- 5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives
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We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.
- Kuninobu, Yoichiro,Nishi, Mitsumi,Kanai, Motomu
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supporting information
p. 8092 - 8100
(2016/09/09)
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- SUBSTITUTED TRICYCLIC BENZIMIDAZOLES AS KINASE INHIBITORS
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Disclosed are substituted tricyclic benzimidazoles compounds as defined herein in formula (I) or pharmaceutically acceptable salts thereof. The compounds of the invention selectively inhibit CDK8 and are therefore useful for treating diseases related to this kinase, especially colorectal and melanoma cancers and other solid and hemathological malignancies, autoimmune diseases and inflammatory diseases. Also disclosed are processes for preparing these compounds.
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Page/Page column 70; 71
(2014/05/24)
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- Synthesis, resolution and structure of axially chiral atropisomeric N- arylimides
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Reported is the synthesis and structures of a new series of axially chiral molecules based on restricted rotation. The ortho-substituted N- arylimides have enantiomeric atropisomers that are stable and separable at room temperature. The compounds are notable for their ease of synthesis as well as positioning of functionality (a carboxylic acid and an amine) in a highly asymmetric configuration. (C) 2000 Published by Elsevier Science Ltd.
- Shimizu, Ken D.,Freyer, Heather O.,Adams, Richard D.
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p. 5431 - 5434
(2007/10/03)
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- BROMINATION OF QUINOLINE DERIVATIVES WITH N-BROMOSUCCINIMIDE. ISOMERIC COMPOSITION OF THE BROMINATION PRODUCTS BY PMR AND GLC
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The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part.Bromo-substituted quinolines can be obtained by this method.The bromination products were identified by PMR spectroscopy.The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule.The compositions of the reaction mixtures were studied by GLC.
- Tochilkin, A. I.,Kovel'man, I. R.,Prokof'ev, E. P.,Gracheva, I. N.,Levinskii, M. V.
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p. 892 - 897
(2007/10/02)
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- Synthesis and Some Properties of A New Class of Six Membered Heteroaromatic Betains, 3H-Pyridobenzotriazin-4-ylium-3-ides
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A series of 3H-pyridobenzotriazin-4-ylium-3-ides has been synthesised by reaction of 8-acylaminoquinolines with O-mesitylenesulphonylhydroxylamine followed by treatment with aqueous alkali.The spectral (u.v., 1H n.m.r., and 13C n.m.r. spectra) and chemical properties (bromination and 1,3-dipolar cycloaddition) of the new mesomeric betains have been investigated.
- Ikeda, Masazumi,Yamagishi, Masafumi,Bayomi, Said M. M.,Miki, Yasuyoshi,Sumida, Yoshio,Tamura, Yasumitsu
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p. 349 - 354
(2007/10/02)
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