36023-01-5Relevant articles and documents
A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers
Shen, Di,Xu, Youjun,Shi, Shi-Liang
, p. 14938 - 14945 (2019)
Axially chiral biaryl scaffolds are essential structural units in chemistry. The asymmetric Pd-catalyzed Suzuki-Miyaura cross-coupling reaction has been widely recognized as one of the most practical methods for constructing atropisomers of biaryls. However, longstanding challenges remain in this field. For example, substrate scope is often narrow and specialized, functional groups and heterocycles can lead to reduced reactivity and selectivity, bulky ortho-substituents are usually needed, and reported methods are generally inapplicable to tetra-ortho-substituted biaryls. We have developed an unprecedented highly enantioselective N-heterocyclic carbene (NHC)-Pd catalyzed Suzuki-Miyaura cross-coupling reaction for the synthesis of atropisomeric biaryls. These reactions enable efficient coupling of aryl halides (Br, Cl) or aryl triflates with various types of aryl boron compounds (B(OH)2, Bpin, Bneo, BF3K), tolerate a remarkably broad scope of functional groups and heterocycles (>41 examples), employ low loading of catalyst (0.2-2 mol %), and proceed under mild conditions. The protocol provided general and efficient access to various atropisomeric biaryls and heterobiaryls in excellent enantioselectivities (up to 99% ee) with no need of using bulky ortho-substituted substrates and was effective for the synthesis of tetra-ortho-substituent biaryls. Moreover, the method was successfully applied to the diastereo- and enantioselective synthesis of atropisomeric ternaphthalenes. Critical to the success of the reaction is the development and application of an extremely bulky C2-symmetric chiral NHC, (R,R,R,R)-DTB-SIPE, as the ligand for palladium. To the best of our knowledge, this is the first highly enantioselective (>90% ee) example of a chiral NHC-metal-catalyzed C(sp2)-C(sp2) cross-coupling reaction.
Regioselective bromination: Synthesis of brominated methoxyquinolines
?akmak, Osman,?kten, Salih
, p. 5389 - 5396 (2017)
Simple synthetic methods are described for the synthesis of valuable polyfunctional brominated methoxyquinolines 10–13, 20–21, and 24–25. Three regioselective routes are described for convenient preparation of brominated methoxyquinolines at the C-2, C-3,
Organic light-emitting compound and organic electroluminescent device containing the same
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Paragraph 0070-0073, (2021/03/13)
The present invention provides an organic light-emitting compound, which is a 5,6-substituted triazinyl quinoline derivative organic light-emitting compound represented by the following chemical formula a. The chemical formula a: When the above-mentioned 5,6-substituted triazinyl quinoline derivative organic light-emitting compound is included in an organic electroluminescent device, the inventioncan excellently meet the appropriate energy level, electrochemical stability and thermal stability.
Enantioselective cross-coupling for axially chiral tetra-ortho-substituted biaryls and asymmetric synthesis of gossypol
Yang, He,Sun, Jiawei,Gu, Wei,Tang, Wenjun
supporting information, p. 8036 - 8043 (2020/05/27)
The axially chiral tetra-ortho-substituted biaryl skeleton exists in numerous biologically important natural products, pharmaceutical molecules, chiral catalysts, and ligands. The efficient synthesis of chiral tetra-ortho-substituted biaryl structures rem
Kinetic Resolution of Axially Chiral 5- or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation
Wang, Jie,Chen, Mu-Wang,Ji, Yue,Hu, Shu-Bo,Zhou, Yong-Gui
supporting information, p. 10413 - 10416 (2016/09/04)
An efficient kinetic resolution of axially chiral 5- or 8-substituted quinoline derivatives was developed through asymmetric transfer hydrogenation of heteroaromatic moiety, simultaneously obtaining two kinds of axially chiral skeletons with up to 209 of selectivity factor. This represents the first successful application of asymmetric transfer hydrogenation of heteroaromatics in kinetic resolution of axially chiral biaryls.
BICYCLIC TRIAZOLES AS PROTEIN KINASE MODULATORS
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Page/Page column 88, (2008/12/05)
The present disclosure provides bicyclic triazole protein kinase modulators and methods of using these compounds to treat diseases mediated by kinase activity.
A contribution to the erythroquine and thalleioquine reaction
Goerlitzer,Weber,Jones
, p. 183 - 187 (2007/10/03)
The 8,8′-biquinoline-5,5′-diones 2A are formed by the erythroquine and thalleioquine reaction from the 6-methoxyquinolines 1 as model compounds. The red substances 2A react with hydrochloric acid to yield the yellow biquinolinedihydrochlorides 3. The structure of 3b dihydrate is determined by X-ray crystal analysis. The redox properties of 2A are investigated by voltammetric methods.
ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
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Page 45, (2010/02/07)
Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.
