- Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction
-
Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20–81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.
- Bunch, Lennart,Cetin, Adnan,Staudt, Markus
-
supporting information
(2022/02/10)
-
- Amination of Aryl Halides Mediated by Electrogenerated Nickel from Sacrificial Anode
-
Electrochemical C(sp2)?N couplings mediated by nickel salts generated from the sacrificial anode has been described for the first time. In this approach, the sacrificial nickel anode is employed as the sole source of nickel and the process, operationally simple to set up, enables the preparation of functionalized arylamine derivatives with moderate to good yields, under mild reaction conditions and without additional ligand. A cooperative process between the two electrodes is involved in the proposed mechanism.
- Daili, Farah,Sengmany, Stéphane,Léonel, Eric
-
p. 2462 - 2469
(2021/06/28)
-
- Catalyst-free photodecarbonylation ofortho-amino benzaldehyde
-
It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.
- Li, Lamei,Wang, Songping,Wei, Wentao,Yan, Ming,Zhou, Jingwei
-
supporting information
p. 3421 - 3426
(2020/06/25)
-
- Photo-induced dealdehyding method
-
The invention provides a photo-induced dealdehyding method, and belongs to the technical field of organic synthesis. The photo-induced dealdehyding method comprises the following steps that a mixtureof a compound shown in the formula I and a solvent are reacted under an inert gas atmosphere and visible light irradiation, a dealdehyding product is obtained, and no photocatalyst is used in the whole process; wherein the structural formula of the formula I shown in the specification, R is a functional group and is selected from hydrogen, methyl, methoxyl, cyano, chlorine, bromine or fluorine. According to the photo-induced dealdehyding method, in the inert gas atmosphere, the compound shown in the formula (I) can be excited to generate carbon-oxygen bond homogeneous cracking through visiblelight irradiation, then free radical migration and double bond displacement are conducted, finally carbon monoxide is removed, aldehyde group removal is completed, no photocatalyst is needed in the whole process, operation is easy and convenient, and conditions are mild.
- -
-
Paragraph 0048-0053; 0090-0095
(2020/06/16)
-
- Bicyclic alkaloid compound, preparation method and applications thereof
-
The present invention relates to a bicyclic alkaloid compound, or a tautomer, a stereoisomer, a racemate, the non-equal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition containing the compound. The invention further discloses uses of the compounds and the pharmaceutical composition thereof as drugs, especially as anti-inflammatory drugs and anti-fibrotic drugs.
- -
-
Paragraph 0183; 0186
(2018/11/03)
-
- Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery
-
Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.
- Devine, William,Woodring, Jennifer L.,Swaminathan, Uma,Amata, Emanuele,Patel, Gautam,Erath, Jessey,Roncal, Norma E.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Mensa-Wilmot, Kojo,Sciotti, Richard J.,Pollastri, Michael P.
-
supporting information
p. 5522 - 5537
(2015/08/03)
-
- COMPOUNDS
-
A compound of formula (I) or a pharmaceutically acceptable salt or prodrug thereof wherein X is N or CH; Q is NR6 or O; A1 and A2 are independently hydrogen or C1-6 alkyl or may together form a carbonyl group; R1 and R2 are independently hydrogen, halogen, CF3, CN, OR7, OR8, NR8R9, NR8COR10, NR8S02R10, S02NR8R9, SO2R10 or C1-6 alkyl optionally and independently substituted by one or more of hydroxyl, C1-6 alkoxy, halogen or NR8 R9; R 3 is hydrogen, halogen, CF3 or OR 7; R4 is hydrogen, halogen, CF3, OR8, NR8R9, NR8COR10, NR8S02R10 or C1-6 alkyl optionally substituted by hydroxyl, C1-6 alkoxy or NR 8 R 9; or when R3 and R4 are positioned ortho and taken together form -0(CH2)mO-, where m is 1-3; R5 is hydrogen or C1-6 alkyl optionally substituted by hydroxyl, C1-6 alkoxy or NR8 R9; R6 is hydrogen or C1-6 alkyl; R7 is hydrogen or C1-6 alkyl optionally substituted by OR8 or NR8R9; R8 is hydrogen, C1-6 alkyl, optionally substituted by hydroxyl or C1-6 alkoxy or C1-3 alkylphenyl wherein said phenyl group is optionally substituted by one or more substituents selected from halogen, C1-6 alkyl, CF3, OR7, NR8R9 or OCF3; or the groups R8 and R9 when they are attached to a nitrogen atom may together form a 5- or 6-membered ring which optionally contains one further heteroatom selected from NR7, S and O said 5 or 6 membered ring being optionally substituted by hydroxyl or C1-6 alkoxy; or the groups R8 and R9 when they are attached to a nitrogen atom may together form an azetidinyl ring optionally substituted by hydroxyl or C1-6 alkoxy; and R10 is C1-6 alkyl or a phenyl group optionally substituted by one or more substituents selected from halogen, C1-6 alkyl, CF3, OCF3 or OR7; and n is 1 or 2. The use of the compounds in treating amyloid disease is also disclosed.
- -
-
Page/Page column 28
(2011/12/04)
-
- COMPOUNDS
-
A compound of formula (I) or a pharmaceutically acceptable salt or prodrug thereof: wherein R1 is CN; R2 is H or F; R3 and R4 are independently hydrogen, fluorine, chlorine or OR5; R5 is hydrogen, C1-6 alkyl, C1-6 alkenyl or C1-6 alkynyl; R6 and R7 are independently hydrogen, halogen, OR8 or NR9R10; R8 is hydrogen or C1-6 alkyl; R9 and R10 are independently hydrogen or C1-6 alkyl; or the groups R9 and R10 when they are attached to a nitrogen atom may together form a 5- or 6-membered ring which optionally contains one further heteroatom selected from NR8, S and O said 5 or 6 membered ring being optionally substituted by hydroxyl or C1-6 alkoxy; or the groups R9 and R10 when they are attached to a nitrogen atom may together form an azetidinyl ring optionally substituted by hydroxyl or C1-6 alkoxy, is provided. The use of such compounds in treating amyloid-related disease is also disclosed.
- -
-
Page/Page column 25-26
(2011/12/04)
-
- Palladium-catalyzed monoamination of dihalogenated benzenes
-
The palladium-catalyzed monoamination of symmetric dibromobenzenes can be performed using a catalyst based on Pd2dba3 and BINAP in the presence of NaO(t-Bu). The analogous transformation of non-symmetric bromoiodobenzenes is most effectively performed with Xantphos as the ligand, while reactions with BINAP were non-selective. These transformations can be scaled uneventfully to >10 g quantities. They do not require drybox or Schlenk techniques, and all reagents are weighed out in air. The resulting monobromoanilines are versatile intermediates for further synthetic transformations.
- Larsen, Simon Birks?,Bang-Andersen, Benny,Johansen, Tommy N?rskov,J?rgensen, Morten
-
p. 2938 - 2950
(2008/09/19)
-
- Novel carbamate and oxamide compounds
-
Disclosed are novel aromatic compounds of the formula(I) described herein, wherein G, E, W, Ar, X, Y and Z are disclosed herein. The compounds are useful for treating cytokine mediated diseases or conditions such as chronic inflammatory diseases. Also disclosed are pharmaceutical compositions containing and processes of making such compounds.
- -
-
-
- Compounds useful as anti-inflammatory agents
-
Disclosed are novel aromatic compounds of the formula(I) wherein G, E, W, Ar, X, Y and Z. The compounds are useful for treating diseases or pathological conditions involving inflammation such as chronic inflammatory diseases. Also disclosed are pharmaceutical compositions containing and processes of making such compounds.
- -
-
-
- Compounds useful as anti-inflammatory agents
-
Disclosed are novel aromatic compounds of the formula(I) wherein G, E, W, Ar, X, Y and Z. The compounds are useful for treating diseases or pathological conditions involving inflammation such as chronic inflammatory diseases. Also disclosed are pharmaceutical compositions containing and processes of making such compounds.
- -
-
-