- One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
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We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.
- Fan, Hui,Xu, Shijie,Yang, Fan,Zhang, Xiaoxiang,Zhao, Xuechun
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supporting information
p. 4555 - 4558
(2021/08/30)
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- Lactam Compound, Preparation Method and Use thereof
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Provided is a lactam compound, a tautomer, a stereoisomer, a racemate, a nonequal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt thereof, or a solvate of the salt of the compound, and a pharmaceutical composition containing the compound. Also provided are the use of such compounds and their pharmaceutical compositions as drugs, especially as antiviral drugs.
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- Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
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In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.
- Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin
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- Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
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Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
- Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
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supporting information
p. 3085 - 3090
(2019/08/07)
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- Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
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A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.
- Li, Quanzhe,Yu, Liuzhu,Wei, Yin,Shi, Min
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p. 9282 - 9296
(2019/08/12)
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- Lewis or Br?nsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif
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We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Br?nsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.
- Wei, Hao-Zhao,Yu, Liu-Zhu,Shi, Min
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p. 135 - 139
(2019/12/26)
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- HETEROARYL INHIBITORS OF PAD4
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The present invention provides compounds useful as inhibitors of PAD4, compositions thereof, and methods of treating PAD4-related disorders.
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Paragraph 00340-00341
(2018/03/28)
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- Chemoselective double annulation of two different isocyanides: Rapid access to trifluoromethylated indole-fused heterocycles
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An unprecedented chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-α]indoles in a single operation from readily available starting materials. Isocyanide insertion into C=O double bonds is disclosed for the first time as indicated by the results of 18O-labeling experiment. A mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides, followed by indole-2,3-epoxide formation and rearrangement.
- Gao, Yuelei,Hu, Zhongyan,Dong, Jinhuan,Liu, Jun,Xu, Xianxiu
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supporting information
p. 5292 - 5295
(2017/11/06)
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- 2-Arylindoles: A new entry to transition metal-free synthesis of 2-aminobenzophenones
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Various 2-aminobenzophenones were synthesized from readily available 2-arylindoles in DMSO under O2 balloon atmosphere. The synthesis was carried out without the aid of a transition metal catalyst or moisture-sensitive organometallic reagents from 2-arylindoles.
- Yu, Jin,Moon, Hye Ran,Min, Beom Kyu,Kim, Jae Nyoung
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supporting information
p. 893 - 897
(2016/06/14)
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- Method for synthesis of sand smooth biphenyl
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The invention discloses a synthetic method of 2-cyano-4'-methylbiphenyl, which adopts paratoluidine and benzoyl chloride as raw materials; a Friedel-Crafts acylation reaction is carried out under a Lewis acid catalysis condition; then a ring-closure reaction of a diazonium salt and a benzene ring is carried out in the presence of sodium nitrite; ring opening is carried out under an alkaline condition to generate a main product as shown in formula VI and a byproduct as shown in formula VII, and the ring-opening products are prepared into salts which are then subjected to separation; and finally, carboxyl groups are converted into cyan groups to obtain 2-cyano-4'-methylbiphenyl. The synthetic method of the invention has the advantages of easily available raw materials, safety, convenience for production management, low cost, reduction in 'three wastes' pollution, byproduct recyclability, and improved atom utilization rate.
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Paragraph 0017; 0018
(2017/03/08)
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- A mild and practical procedure for synthesis of substituted 2-aminobenzophenones
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Abstract A convenient three-step procedure has been developed for synthesis of substituted 2-aminobenzophenones from substituted anilines. The anilines are first protected as acetanilides, by reaction with acetic anhydride. These are then benzoylated with (trichloromethyl)benzene in the presence of aluminium-generated 2-acetamidobenzophenone. Finally, removal of the acetyl group from the amino group provides the substituted 2-aminobenzophenones in moderate to good yields.
- Ma, Er-Qian,Wang, Ping,Li, Pei-He,Mo, Li-Ping
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p. 6433 - 6441
(2015/08/18)
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- Fries-type rearrangement of acylanilides in the presence of ytterbium triflate
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Ytterbium triflate has been used to catalyse the Fries-type rearrangement of various acylanilides with moderate yields when lithium perchlorate was used as co-catalyst.
- Su, Weike,Jin, Can
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p. 611 - 613
(2007/10/03)
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- Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof
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The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).
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Page/Page column 15
(2010/02/06)
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- Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors
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A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-1enzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo.
- Hu, Wenhui,Guo, Zongru,Chu, Fengming,Bai, Aiping,Yi, Xiang,Cheng, Guifang,Li, Jing
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p. 1153 - 1160
(2007/10/03)
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- Tetrazoles: XXXV. Synthesis of 3H-1,3,4-Benzotriazepines from 5-Aryltetrazoles
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Reaction of 5-aryltetrazoles with N,N′-bis(p-tolyl)terephthalimidoyl dichloride under conditions of phase-transfer catalysis yields isomeric N-imidoyltetrazoles whose thermolysis results in formation of 3H-1,3,4-benzotriazepines. The latter are hydrolyzed by the action of hydrochloric acid to afford terephthalic acid and the corresponding aminobenzophenone.
- Artamonova,Koldobskii
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p. 1767 - 1770
(2007/10/03)
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- Intramolecular Nitrene Insertion into Aromatic and Heteroaromatic Rings. Part 9. Synthesis of 2-Azidodiphenylmethanes and the Kinetics of their Thermal Decomposition in Solution
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The synthesis of some new o-azidodiphenylmethanes 3b, 10, 15, 18, 21 and 22 is described.The first-order kinetics of the thermal decomposition in trichlorobenzene of these and some previously studied azides (3a, 3c and 3d) has been studied in the range 140-180 K.The initial step is evolution of nitrogen and formation of a nitrene intermediate, which reacts to give a 10H-azepinoindole together with some amine.Rate constants for the first step were compared with those for product formation and show it to be the rate-determining factor.Electron-donating substituentspara to the azide group stabilise the incipient nitrene by resonance interactions (rate constants correlate with ?R+) yielding higher proportions of amine products, which result from the spin forbidden singlet-triplet nitrene transition.Substituents at the 4'-position influence the nature of the products but not decomposition rates.A new compound, 1a-methoxy-1a,9b-dihydro-1H-cyclopropapyridolindole (28), is obtained from 2-azido-4'-methoxydiphenylmethane (3d) in addition to the expected azepinoindole and amine.Kinetic measurements show that it is an intermediate in one, but not the sole, route to formation of 8-methoxyazepinoindole 27 from 3d.
- Jones, Gurnos,Long, Brian D.,Thorne, Melanie P.
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p. 903 - 913
(2007/10/02)
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- PHOTOBEHAVIOUR OF N-ARYL AMIDES IN MICELLE
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Photoreaction of N-aryl amides in micellar environment of SDS leading to the high yield and selective formation of 2-aminobenzophenone as a major product is described.
- Singh, A. K.,Raghuraman, T. S.
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p. 485 - 490
(2007/10/02)
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- SURFACE PHOTOCHEMISTRY: THE AMIDE PHOTO-FRIES REARRANGEMENT
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The Photo-Fries rearrangement of eight anilides on the surface of dry silica gel has been examined.The rearrangement occurs quite cleanly, giving somewhat more of the para isomer than that obtained in methanolic solution.A test for intermolecularity on the silica gel surface showed that, as in solution, the radical pair intermediates do not separate.This contrasts with the behaviour of a previously reported dibenzyl ketone derivate.
- Magdy, M.,Malik, Abdel-,Mayo, Paul de
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p. 1275 - 1278
(2007/10/02)
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- Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups
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According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.
- Hellwinkel, Dieter,Laemmerzahl, Frank,Hofmann, Gunter
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p. 3375 - 3405
(2007/10/02)
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- HETEROCYCLIC SYNTHESES VIA CARBANIONICALLY INDUCED REARRANGEMENT REACTIONS
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The easily occuring -migrations of sulfonyl and carbonyl functions to neighboring phenyl anions can be utilized for ring expansions by one benzo unit when suitably tailored precursor heterocycles are used.Thus, the 1,2- benzisothiazol dioxide systems 8 and 17 can be transformed into dibenzothiazepin dioxides 12 and 21, respectively, whereas the dibenzo- and 1,2,4-benzothiazin dioxide models 35 and 46 give rise to the tribenzothiazocin dioxide and dibenzothiadiazocin dioxide systems 38 and 47, respectively.Unexpected formations of heterocyclic systems, namely, spirobenzoxazin-5,1'(3H)-isobenzofuran> 55, 3,1-benzoxazin 62, and phenanthridinium-salt 70 took place when phtalimide 52, dibenzoylaniline 56, and biphenylylbenzamide 65 were reacted with t-BuLi.
- Hellwinkel, Dieter,Lenz, Ruediger,Lammerzahl, Frank
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p. 2073 - 2084
(2007/10/02)
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