- Site-Specific Synthesis of Carbazole Derivatives through Aryl Homocoupling and Amination
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We synthesized various carbazoles from anilines through a three-step process with good overall yields (up to 48percent). This process comprises N -acetylation, copper(0)-mediated Ullmann homocoupling, and acid-mediated intramolecular amination. It permits various functional groups on the substrate. Scale-up of the developed three-step synthetic route to carbazoles was also demonstrated.
- Baek, Junghyun,Ban, Jaeyoung,Lim, Minkyung,Rhee, Hakjune,Shabbir, Saira
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- Synthesis method of o-bromo-p-fluoroacetyl aniline
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The invention relates to a synthesis method of o-bromo-p-fluoroacetyl aniline, and belongs to the technical field of synthesis of chemical intermediates. According to the preparation method, potassium fluoride and parachloronitrobenzene are taken as starting raw materials, halogen exchange, reduction, acylation reaction and bromination reaction are carried out, then the o-bromo-p-fluoroacetyl aniline is prepared, and the synthesis method which is high in operability, high in product yield and high in purity is provided for synthesis of the o-bromo-p-fluoroacetyl aniline.
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- 4 - Fluorine substituted aryl amine compound and synthesis method thereof
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The invention discloses a synthesis method of 4 -fluorine substituted aryl amine compound, which comprises the following steps: 1) taking acyl-protected phenylhydroxylamine as a substrate, and generating 4 -fluorine substituted aniline compound under basic conditions by taking sulfonyl fluoride as a fluorine source in a polar solvent. 2) The deprotection is carried out under dilute acid conditions or Pd by catalytic hydrogenation to give the 4 - fluorine-substituted aryl amine compound. 4 - Fluorine substituted aniline compounds which are synthesized by the invention greatly increase the lipophilic property due to the introduction of fluorine atoms, and can be widely applied to preparation of fluorine-containing drugs and pesticide and dye intermediates. , The adopted raw materials are industrial products, are cheap and easily available, and are commercially available. 4 - Fluoroaryl aniline prepared by the method is high in yield, and the product with the purity 90% can be obtained in a yield of more than ≥ 99%. The method is simple to operate and low in cost, is very suitable for industrialization, and can be widely popularized and used.
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Paragraph 0063-0065
(2021/09/22)
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- QUINOXALINE DERIVATIVES
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The present invention relates to compounds according to general formula (I), which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.
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Page/Page column 59
(2021/07/24)
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- Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates
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ortho -C-H bond halogenation of anilides and N -aryl carbamates using easily available N -halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.
- Kianmehr, Ebrahim,Afaridoun, Hadi
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p. 1513 - 1523
(2020/12/14)
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- Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source
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A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.
- Zheng, Yan,Dong, Mengke,Qu, Erdong,Bai, Jin,Wu, Xiao-Feng,Li, Wanfang
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supporting information
p. 16219 - 16224
(2021/10/06)
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- SUBSTITUTED TRIAZOLO QUINOXALINE DERIVATIVES
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The present invention relates to compounds according to general formula (I) which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.
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Page/Page column 80
(2020/02/14)
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- Rhodium-Catalyzed ortho-Bromination of O-Phenyl Carbamates Accelerated by a Secondary Amide-Pendant Cyclopentadienyl Ligand
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It has been established that a newly developed cyclopentadienyl rhodium(III) [CpARhIII] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.
- Tanaka, Jin,Shibata, Yu,Joseph, Anton,Nogami, Juntaro,Terasawa, Jyunichi,Yoshimura, Ryo,Tanaka, Ken
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supporting information
p. 5774 - 5779
(2020/05/08)
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- Preparation method of 2-(3,4)-dichlorophenyl-4-fluoroaniline
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The invention discloses a preparation method of 2-(3,4)-dichlorophenyl-4-fluoroaniline, comprising the steps of (1) dissolving 2-bromo-4-fluoroaniline in dichloroethane, dropwise adding acetic anhydride to obtain the compound 2-bromo-4-fluoroacetanilide; (2) dissolving the product of step (1) and 3,4-dichlorobromobenzene in an organic solvent, and dropwise adding Rieke Zn; in another reaction vessel, dissolving CuBr Sme2 in the same organic solvent, mixing, adding an oxidant for reaction, filtering the reacted liquid via silica gel, distilling in vacuum, and carrying out column chromatographyto obtain 2-(3,4-dichlorophenyl)-4-fluoroacetanilide; (3) adding the product of step (2) into the reaction vessel, adding methanol to allow full dissolution, and dropwise adding concentrated sulfuricacid slowly; when the materials completely react, pouring the mixed solution into ice water while it is hot for the purpose of quenching. A copper reagent that is low in price and easy to obtain is used to replace toxic heavy metals such as palladium; the domestic blank of studies on bixafen is filled; the foreign monopoly for bixafen is broken; progress of leaf blight and rust disease can be controlled.
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Paragraph 0022; 0023
(2018/09/13)
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- Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
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A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
- Li, Ze-lin,Sun, Kang-kang,Cai, Chun
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supporting information
p. 5433 - 5440
(2018/08/12)
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- A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst
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A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.
- Singh, Harshvardhan,Sen, Chiranjit,Sahoo, Tapan,Ghosh, Subhash Chandra
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p. 4748 - 4753
(2018/09/06)
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- Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
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Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
- Kathiravan, Subban,Nicholls, Ian A.
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supporting information
p. 7031 - 7036
(2017/05/29)
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- Combined C-H functionalization/C-N bond formation route to carbazoles
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A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen. Copyright
- Tsang, W. C. Peter,Zheng, Nan,Buchwald, Stephen L.
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p. 14560 - 14561
(2007/10/03)
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