51054-99-0Relevant academic research and scientific papers
FLUOROALKYL-OXADIAZOLES AND USES THEREOF
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Paragraph 00263-00264, (2021/06/26)
Provided herein are compounds identified as inhibitors of HDAC6 activity that can be used to treat various diseases and disorders.
Borylation of Unactivated C(sp3)-H Bonds with Bromide as a Traceless Directing Group
Zhang, Ge,Li, Meng-Yao,Ye, Wen-Bo,He, Zhi-Tao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 2948 - 2953 (2021/05/05)
A palladium-catalyzed alkyl C-H borylation with bromide as a traceless directing group is described, providing a convenient approach to access alkyl boronates bearing a β-all-carbon quaternary stereocenter. The protocol features a broad substrate scope, excellent site selectivity, and good functional group tolerance.
INDOLE AHR INHIBITORS AND USES THEREOF
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Paragraph 00395, (2020/05/21)
The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.
Synthesis of Tetrahydronaphthyridines from Aldehydes and HARP Reagents via Radical Pictet-Spengler Reactions
Jackl, Moritz K.,Kreituss, Imants,Bode, Jeffrey W.
supporting information, p. 1713 - 1715 (2016/05/19)
The combination of aldehydes with newly designed HARP (halogen amine radical protocol) reagents gives access to α-substituted tetrahydronaphthyridines. By using different HARP reagents, various regioisomeric structures can be prepared in a single operation. These products, which are of high value in medicinal chemistry, are formed in a predictable manner via a formal Pictet-Spengler reaction of electron-poor pyridines that would not participate in the corresponding polar reactions.
One-pot synthesis of new aza- and diaza-aminophenanthrenes
Rochais, Christophe,Yougnia, Rodrigue,Cailly, Thomas,Sopková-De Oliveira Santos, Jana,Rault, Sylvain,Dallemagne, Patrick
scheme or table, p. 5806 - 5810 (2011/08/09)
The synthesis of a series of benzo(iso)quinoline and phenanthroline derivatives has been achieved using an efficient one-pot procedure. It proceeds through a Suzuki-Miyaura cross-coupling followed by a Dieckmann-Thorpe ring closure under microwave irradia
Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: Method and mechanistic study
Chaumontet, Manon,Piccardi, Riccardo,Audic, Nicolas,Hitce, Julien,Peglion, Jean-Louis,Clot, Eric,Baudoin, Olivier
supporting information; experimental part, p. 15157 - 15166 (2009/03/12)
An efficient catalytic system has been developed for the synthesis of benzocyclobutenes by C-H activation of methyl groups. The optimal conditions employed a combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3 as the base, and DMF as solvent. A variety of substituted BCB were obtained under these conditions with yields in the 44-92% range, including molecules that are hardly accessible by other methods. The reaction was found limited to substrates bearing a quaternary benzylic carbon, but benzocyclobutenes bearing a tertiary benzylic carbon could be obtained indirectly from diesters by decarboxylation. Reaction substrates bearing a small substituent para to bromine gave an unexpected regioisomer that likely arose from a 1,4-palladium migration process. The formation of this "abnormal" regioisomer could be suppressed by introducing a larger subsituent para to bromine. DFT(B3PW91) calculations on the reaction of 2-bromo-tert-butylbenzene with Pd(PtBu3) with different bases (acetate, bicarbonate, carbonate) showed the critical influence of the coordination mode of the base to induce both an easy C-H activation and to allow for a pathway for 1,4-palladium migration. Carbonate is shown to be more efficient than the two other bases because it can abstract the proton easily and at the same time maintain κ1-coordination without extensive electronic reorganization.
