- Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
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An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N–N and N–C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope.
- Li, Zhen-Hua,Sun, Xiao-Meng,Qin, Jin-Jing,Tan, Zhi-Yong,Wang, Wen-Biao,Ma, Yao
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- Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds
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The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
- Suárez-Pantiga, Samuel,Hernández-Ruiz, Raquel,Virumbrales, Cintia,Pedrosa, María R.,Sanz, Roberto
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supporting information
p. 2129 - 2133
(2019/01/25)
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- Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
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The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
- Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
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supporting information
p. 2897 - 2901
(2018/05/29)
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- A benzhydryl radical based on the room temperature of the organic light-emitting material and using the material preparation of organic electroluminescent device
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A benzhydryl radical based on the stability of the organic light-emitting material at room temperature and using the material preparation of the organic electroluminescent device, which belongs to the field of organic light-emitting technology. The present invention in the preparation of the organic light-emitting material, the center of the common characteristic is the carbon free radical, is composed of two C - C covalent bond and a C - N to form a covalent bond. Stability is the light-emitting free radical material in the application of the key nature, connected to the electronic group conducive to stable free radical, in this invention through the nitrogen-containing heterocyclic carbazole, indole, dimethyl acridine and the like in the electronic group to the nitrogen atom is connected directly to the benzyl group, to obtain a stable benzhydryl radical, its stability and PTM, compared with the TTM is greatly improved, and has a room temperature fluorescent. The preparation of the material of the organic electroluminescent device using double thread condition exciton light-emitting, can avoid the traditional organic electroluminescent device in the use of the triplet state exciton, the maximum external quantum efficiency of the device is 0.66%.
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Paragraph 0039; 0040; 0041
(2018/07/30)
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- Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
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The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
- Roscales, Silvia,Csák?, Aurelio G.
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supporting information
p. 1667 - 1671
(2018/03/23)
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- 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities
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Because N-arylation of isatin only worked with iodoferrocene (and in low yield), we employed N-arylation of 2-aminophenones and subsequent oxidative cyclization to access various N-arylated isatins. In the course of this work, we observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2,3-b]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β Haspin and leishmanial CK1. The biological results are reported.
- Brikci-Nigassa, Nahida Mokhtari,Bentabed-Ababsa, Ghenia,Erb, William,Chevallier, Floris,Picot, Laurent,Vitek, Lucille,Fleury, Audrey,Thiéry, Valérie,Souab, Mohamed,Robert, Thomas,Ruchaud, Sandrine,Bach, Stéphane,Roisnel, Thierry,Mongin, Florence
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p. 1785 - 1801
(2018/03/12)
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- Pd/AlO(OH): A Heterogeneous, Stable and Recyclable Catalyst for N-Arylation of Aniline Under Ligand-Free Aerobic Condition
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Abstract: Many synthetic methods have been reported to construct an aryl-nitrogen bond. But they mainly suffer from the usage of expensive ligands. Herein, we report highly effective, heterogeneous, reusable and ligand-free nanocatalyst for the Buchwald-Hartwig coupling reaction under aerobic condition. Wafer-like structure with nano-porous nature of AlO(OH) was identified with TEM and BET surface area analyses. Zero valent Pd nanoparticles (with less than 10?nm crystallite size which strongly evident from TEM analysis) were observed in XRD pattern, which was further confirmed by XPS studies. The reaction conditions were optimized and the scope of the reaction was extended with various aryl halides and aniline using low amount of Pd (0.31?mol%) based heterogeneous catalyst. Heterogeneity, reusability and stability (confirmed by XRD) were found to be reasonable. Use of meagre amount of Pd and the ligand-free aerobic condition make this system economically as well as environmentally feasible. Graphical Abstract: [Figure not available: see fulltext.].
- Ganesh Babu, Sundaram,Emayavaramban, Balakumar,Jerome, Peter,Karvembu, Ramasamy
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p. 2619 - 2629
(2017/09/06)
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- N-(Pyridin-2-yl)benzamide: Efficient ligand for the nickel catalyzed Chan-Lam cross-coupling reaction
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An efficient protocol for the Chan-Lam cross-coupling reactions of arylboronic acids with aryl or alkyl amines has been developed by employing simple N-(pyridin-2-yl)benzamide ligand with Ni(OAc)2·4H2O in the presence of TMG base. The reaction proceeded well with high yields by employing various N-nucleophiles at low catalytic loadings.
- Keesara, Srinivas
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p. 6685 - 6688
(2016/01/28)
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- Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones
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An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.
- Huang, Jinbo,Mao, Tingting,Zhu, Qiang
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supporting information
p. 2878 - 2882
(2014/05/20)
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- Intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF: A new synthesis of indole derivatives
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A new synthesis of indole derivatives has been achieved through intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF. The reaction probably proceeds via an α-amino alkyl radical pathway.
- Wei, Wen-Tao,Dong, Xue-Jiao,Nie, Shao-Zhen,Chen, Yan-Yan,Zhang, Xue-Jing,Yan, Ming
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supporting information
p. 6018 - 6021
(2014/01/06)
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- Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins
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A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright
- Liu, Yong,Chen, Hui,Hu, Xiong,Zhou, Wang,Deng, Guo-Jun
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supporting information
p. 4229 - 4232
(2013/07/26)
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- Synthesis of N-arylindazoles and benzimidazoles from a common intermediate
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A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields. The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles. This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals.
- Wray, Brenda C.,Stambuli, James P.
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supporting information; experimental part
p. 4576 - 4579
(2010/11/20)
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- ANTI-PARASITIC COMPOUNDS AND METHODS OF THEIR USE
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The present invention provides a novel class of compounds that disrupt the parasitic infectious life cycle and serve as promising agents for anti-parasitic therapy.
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Page/Page column 29
(2008/06/13)
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- A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et
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The condensation of 2-anilinoacetophenone with RFCO2Et (RF = CF2H, CF3, C2F5) in the presence of LiH in THF affords the corresponding N -phenyl-2-polyfluoroalkyl-4-quinolones in
- Usachev, Boris I.,Sosnovskikh, Vyacheslav Ya.
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p. 1393 - 1395
(2007/10/03)
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- Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi
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We have synthesized a library of thiosemicarbazones and screened them against three parasitic cysteine proteases, cruzain, falcipain-2, and rhodesain, and against the respective parasite sources of these three proteases, Trypanosoma cruzi, Plasmodium falciparum, and Trypanosoma brucei. The screens identified compounds that were effective against the enzymes and the parasites but also some compounds that were parasiticidal despite a lack of activity against the proteases. Several compounds were effective in killing all tested parasites. These promising lead compounds were tested for general toxicity in mice, and only one produced observable toxicity after 62 h. Our results suggest that thiosemicarbazones represent validated drug leads that kill several species of protozoan parasites through the inhibition of cysteine proteases as well as other novel targets.
- Greenbaum, Doron C.,Mackey, Zachary,Hansell, Elizabeth,Doyle, Patricia,Gut, Jiri,Caffrey, Conor R.,Lehrman, Julia,Rosenthal, Philip J.,McKerrow, James H.,Chibale, Kelly
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p. 3212 - 3219
(2007/10/03)
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- Thermal decomposition of tert-butyl o-(phenoxy)- and o-(anilino)-phenyliminoxyperacetates
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Some o-phenoxy- and o-anilino-substituted aryliminyl radicals have been generated by thermal decomposition of suitable tert-butyl iminoxyperacetates. The iminyls show no disposition to give 7-membered cyclisation on the phenyl group. In some cases, products have been found that can be rationalised through a 1,6-spirocyclisation of the iminyl radicals followed by homolytic 1,5-migration of the phenyl group from the aminic to the iminic nitrogen: this seems to be the first instance of such a process. Evidence has been found for the formation of imines through hydrogen abstraction by the iminyls; with two o-phenoxy-substituted peresters these imines have been unexpectedly isolated. The reactions have also afforded significant - in some cases major - amounts of other products (acridine, quinazolinone and indole derivatives) presumably deriving from carbon radicals: mechanisms are suggested to account for the formation of these compounds. The structure of the quinazolinone compound has been determined by X-ray crystallographic analysis.
- Calestani, Gianluca,Leardini, Rino,McNab, Hamish,Nanni, Daniele,Zanardi, Giuseppe
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p. 1813 - 1824
(2007/10/03)
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- Acat inhibitors for treating hypocholesterolemia
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The present invention are novel amino acid amide compounds of the following general formula which inhibit the enzyme acylcoenzyme A:cholesterol acyltransferase: STR1 wherein R is phenyl or 1- or 2-naphthyl which are unsubstituted or may be substituted; R1 is hydrogen or a straight or branched alkyl group having from 1 to 6 carbon atoms; R2 is hydrogen, an aliphatic group, an aromatic group, an aralkyl or diarylalkyl group or R1 and R2 form a carbocyclic group; R3 is hydrogen, an aliphatic group, an aralkyl group wherein the alkyl moiety may contain a carbocyclic entity; R4 is hydrogen, an aliphatic group, SO2 R14, --C(=S)NHR15, --CO2 R15, --COR18, or --C(=O)NHR15 wherein R14 is morpholino, phenyl or substituted phenyl; R15 is an alkyl group, phenyl or phenylalkyl wherein the phenyl group may be substituted; and R18 is the same is R15 or is halo-substituted alkyl, 9-fluoroenylmethylene or pyrrolidino.
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- 12-Organyldibenzazocine-5,7-diones
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The title compounds 10, 23 are formed in low yields on treatment of 2,2'-organylimino-bisbenzoic acid esters 8 with methyllithium, but in high yields in the intramolecular ester condensation with sodium hydride of triarylamines 12, containing o-acetyl-, a
- Hellwinkel, Dieter,Ittemann, Peter
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p. 3165 - 3197
(2007/10/02)
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