- A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids
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A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.
- Liu, Li,Li, Yue,Huang, Tiao,Kong, Dulin,Wu, Mingshu
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p. 2321 - 2328
(2021/09/22)
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- A Benzisoelenazolone modified pyrrole methyl ester substituted indole ketone compound and use thereof
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The invention discloses a benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and a use thereof. The invention depends on and claims the priority of a Chinese patent application 201110105248.0 submitted on April 26, 2011. Through reference, all contents of the Chinese patent application 201110105248.0 are incorporated into the invention. The benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound is shown in the general formula I. The 2-indolone compound provided by the invention has excellent antitumor activity and can be widely used for preparation of antitumor drugs.
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Paragraph 0117-0118; 0194-0196
(2016/10/08)
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- Selective reduction of carbonyl groups in the presence of low-valent titanium reagents
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The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.
- Lin, Wei,Hu, Ming-Hua,Feng, Xian,Fu, Lei,Cao, Cheng-Pao,Huang, Zhi-Bin,Shi, Da-Qing
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p. 2238 - 2242
(2014/04/17)
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- Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate
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A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.
- Dinesh, Bhima Reddy,Baba, A. Ramesha,Sankar, K. Udaya,Gowda, D. Channe
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experimental part
p. 287 - 288
(2009/04/07)
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- Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols
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A new effective catalytic system consisting of [Cp*RhCl 2]2/K2CO3 (Cp* = pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [Cp*RhCl2]2 (5.0% Rh) and K 2CO3 (10%) in acetone gives 3,4-dihydro-2(1H)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system.
- Fujita, Ken-Ichi,Takahashi, Yoshinori,Owaki, Maki,Yamamoto, Kazunari,Yamaguchi, Ryohei
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p. 2785 - 2788
(2007/10/03)
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- An improved procedure for the regiospecific synthesis of electron deficient 4- and 6-substituted isatins
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The regiospecific synthesis of 4- and 6-substituted isatins 5a-g in four steps from halonitrobenzenes 1a-g has been investigated for a variety of substrates (Scheme 1). The procedure makes use of readily available, easily handled materials and in most cases purification of neither intermediates nor final products is required. Yields of isatins are between 26 and 75% (Table 1). Improved yields of known isatins are reported as well as the syntheses of previously unreported isatins. This method, taken together with known procedures, provides for the synthesis of the full complement of isatin regioisomers.
- Kraynack, Erica A.,Dalgard, Jackline E.,Gaeta, Federico C. A.
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p. 7679 - 7682
(2007/10/03)
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- A general oxindole synthesis
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A general synthesis of indol-2(3H)-ones (oxindoles), was developed based on the addition of dimethyl malonate to commercially available halonitrobenzenes. The advantage of this route over many other oxindole syntheses was the regiochemical control of the substitution pattern on the aromatic ring.
- Quallich,Morrissey
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- Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines
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Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).
- Clark,Muchowski,Fisher,Flippin,Repke,Souchet
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p. 871 - 878
(2007/10/02)
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- 1,3-dicarboxamide-oxindoles as antiinflammatory agents
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1,3-Dicarboxamidooxindoles as antiinflammatory agents prepared by reaction of the 1-carbamoyloxindole with an isocyanate or by aminolysis of the corresponding alkyl 1-carbamoyloxindole-3-carboxylate.
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- Analgesic and anti-inflammatory 1-acyl-2-oxindole-3-carboxamides
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Certain new 2-oxindole-3-carboxamide compounds having an acyl substituent at the 1-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for acute administration for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and also for chronic administration for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.
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- 1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
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- Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. Certain 2-oxindole compounds unsubstituted at the 1-position but having an acyl substituent at C-3 of the formula STR1 and the base salts thereof, wherein X is hydrogen, 5-fluoro, 5-chloro or 5-trifluoromethyl; Y is hydrogen, 6-fluoro, 6-chloro or 6-trifluoromethyl; and R1 is benzyl, furyl, thienyl or thienylmethyl; provided that when X and Y are both hydrogen, R1 is not benzyl are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.
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- Process for making 2-oxindole-1-carboxamides and intermediates therefor
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Preparation of 2-oxindole-1-carboxamides by reaction of 2-oxindoles with chlorosulfonyl isocyanate to produce novel N-chlorosulfonyl-2-oxindole-1-carboxamides which are then hydrolyzed to 2-oxindole-1-carboxamides useful as intermediates for analgesic and antiinflammatory agents.
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- Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
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Certain novel 2-oxindole compounds, having an acyl substituent at both the 1-position and the 3-position, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and antiinflammatory agents in mammalian subjects. These 1,3-diacyl-2-oxindole compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases such as rheumatoid arthritis and osteoarthritis.
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- N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
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Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.
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- α-Nitroarylation of Ketones and Esters: An Exceptionally Facile Synthesis of Indoles, 2-Indolinones, and Arylacetic Acids
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Silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of fluoride ion sources to give dihydroaromatic nitronates which are readily oxidized to α-nitroaryl carbonyl compounds by DDQ or Br2.These versatile intermediates are readily converted into indoles or 2-indolinones by reductive cyclization.Since halogen substituents on the aromatic ring are not displaced in the initial alkylation reaction, nucleophilic substitution of these groups, followed by functional group manipulations of the nitro group, permits easy access to indoles, 2-indolinones, and arylacetic acids with varied substitution patterns.
- RajanBabu, T. V.,Chenard, Bertrand L.,Petti, Michael A.
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p. 1704 - 1712
(2007/10/02)
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- 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents
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Certain new 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and in alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.
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- MONO(m-SUBSTITUTED) CHLOROACETYLDIARYLAMINES IN THE STOLLE REACTION
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The effect of substituted (OCH3, Cl) on the ratio of the isomeric N-aryloxindoles formed in the Stolle reaction from mono(m-substituted) chloroacetyldiarylamines was studied.It was shown by means of gas-liquid chromatography (GLC) and PMR spectroscopy that in the case of the methoxy group electrophilic substitution occurs only in the ring activated by the substituent.The presence of a halogen atom leads only to 1-(m-chlorophenyl)oxindole.The results show that high selectivity of the attack by the carbonium ion on the phenyl rings with electron-donor and electron-acceptor substituents is also retained in the case of intramolecular electrophilic substitution under conditions of kinetic control.
- Przheval'skii, N. M.,Grandberg, I. I.
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p. 716 - 719
(2007/10/02)
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- Oxindoles as sleep-inducers
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Sleep inducers of the formula: STR1 wherein R is hydrogen or halo of atomic weight of from 18 to 36, R' is hydrogen, halo or CF3 and R° is hydrogen or lower alkyl. Preparation by cyclizing a 2-nitro-phenylacetic acid is also disclosed.
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