34943-91-4

Upstream product

• 84258-40-2 1-Benzyl-7-chloro-3-methyl-1,4,5,6-tetrahydro-indol-2-one 
• 84258-44-6 1-Benzyl-7-bromo-3-methyl-1,4,5,6-tetrahydro-indol-2-one 
• 17017-58-2 1-benzyl-3-methyl-1H-indole 
• 887235-16-7 S-(4-pentynyl) N-benzyl-N-(2-vinylphenyl)carbamothioate 
• 108-98-5 thiophenol 
• 40800-64-4 3-methylsulfanyl-1,3-dihydroindol-2-one 
• 27326-43-8 2-vinylbenzoic acid 
• 758640-21-0 N-Benzylaniline 
• 1613248-88-6 tert-butyl 3-(benzyl(phenyl)amino)-3-oxopropanoate 
• 1613248-89-7 tert-butyl 3-(benzyl(phenyl)amino)-2-methyl-3-oxopropanoate 
• 67-56-1 methanol 
• 7135-32-2 1-benzylindolin-2-one 
• 64-17-5 ethanol 
• 13939-06-5 molybdenum hexacarbonyl 

Downstream Products

• 47529-22-6 1-benzyl-3-methyl-3-(3-morpholin-4-yl-propyl)-1,3-dihydro-indol-2-one 
• 799561-13-0 C₃₉H₄₀N₂O₄ 
• 876337-60-9 carbonic acid 1-benzyl-3-methyl-1H-indol-2-yl ester phenyl ester 
• 1092719-31-7 1-benzyl-3-methylindol-2-yl dimethylcarbamate 
• 1222484-89-0 C₂₂H₂₀N₂O₂ 
• 1269105-91-0 1-benzyl-3-methyl-3-(phenylamino)indolin-2-one 
• 1269105-71-6 1-benzyl-3-(hydroxy(phenyl)amino)-3-methylindolin-2-one 
• 886225-87-2 (S)-3-allyl-1-benzyl-3-methylindolin-2-one 
• 34944-05-3 1-benzyl-3-hydroxy-3-methyl-2-oxo-2,3-dihydroxyindole 
• 1351204-70-0 1-benzyl-3-(1-(benzyloxy)allyl)-3-methylindolin-2-one 
• 1620145-02-9 tert-butyl (1,1'-dibenzyl-3'-methyl-2,2'-dioxo-[3,3'-biindolin]-3-yl)carbamate 
• 1620145-26-7 tert-butyl (1,1'-dibenzyl-3'-methyl-2,2'-dioxo-[3,3'-biindolin]-3-yl)carbamate 
• 1620145-04-1 tert-butyl (1,1'-dibenzyl-5-fluoro-3'-methyl-2,2'-dioxo-[3,3'-biindolin]-3-yl)carbamate 
• 1620145-05-2 tert-butyl (1,1'-dibenzyl-5-chloro-3'-methyl-2,2'-dioxo-[3,3'-biindolin]-3-yl)carbamate 

Relevant academic research and scientific papers

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). Thisin situgenerated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.

Reagent-Controlled Reversal of Regioselectivity in Nucleophilic Fluorination of Spiro-epoxyoxindole: Synthesis of 3-Fluoro-3-hydroxymethyloxindole and 3-Aryl-3-fluoromethyloxindole

A convenient and metal/catalyst-free approach for the reversal of regioselectivity in nucleophilic fluorination of a wide range of spiro-epoxyoxindoles has been reported simply by altering the nucleophilic fluoride reagents. Py·(HF)x-mediated f

Reactions of 5-aryloxazolidines with CH-acidic compounds

5-Aryloxazolidines react with active methylene compounds in the presence of catalytic magnesium ethoxide to give methylene-linked 1,3-dicarbonyl compounds, while the similar reaction with 2-oxindoles results in 3-methyl derivatives.

Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source

We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.

Green method for preparing oxindole derivative

The invention relates to the technical field of green organic synthesis, and provides a green method for preparing oxindole derivatives, which comprises the following steps: taking indole compounds with different functional groups as raw materials, under the conditions of room temperature, opening and neutral, adopting MBrx (M is Fe,Fe,Ce and the like) as a catalyst with X equal to 2 or 3, and adopting hydrogen peroxide as a sole oxidant to generate active bromine (RBS) in situ, and catalytically synthesizing the oxindole derivative. According to the method disclosed by the invention, MBrx (such as FeBr2, CeBr3 and the like) is used as the catalyst, so that an expensive or complex catalyst is avoided, and the method is green, environment-friendly, safe, simple, efficient, mild in reaction condition and wide in substrate application range, has a relatively good application prospect and is expected to be widely applied to organic synthesis, fine chemical engineering and pharmaceutical industry.

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles

A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.

Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles

In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which is based on the FeCl3 catalyst and the t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity. The generality of the conditions was proven by reacting various substituted phenols, naphthols, and tyrosine derivatives with 3-alkyloxindoles. To apply the chemistry for the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives, the reaction conditions were modified [Fe(O2CCF3)3 catalyst, t-BuOOt-Bu, HFIP, 70 °C], and amino acids with acid-stable N-protecting groups were used.

Indium Catalyzed Sequential Regioselective Remote C?H Indolylation and Rearrangement Reaction of Peroxyoxindole

Indium-catalyzed sequential remote C?H functionalization (C-6 position) and C3-indolylation of peroxyoxindole using indole is described for the synthesis of terindolinone derivatives. Whereas, N-substituted 3-phenyl peroxyoxindole derivatives undergoes consecutive skeletal rearrangement to generate transient carbocation, which has been trapped with indole nucleophile to generate 2-(1H-indol-3-yl)-4-alkyl-benzo[b][1,4]oxazin-3(4H)-one derivatives. In contrast with Indium (III) Chloride, FeCl3 ? 6H2O facilitates oxidative cleavage of the peroxyoxindole (Hock cleavage) and further reaction with indole to afford biologically important trisindoline derivatives. A plausible mechanism has been proposed for these reactions with experimental evidences. (Figure presented.).

Reductive aromatization of oxindoles to 3-substituted indoles

A practical and scalable approach for the synthesis of 3-substituted indoles is delineated via hydride nucleophilic addition to 3-substituted-2-oxindoles. The reaction proceeds through reductive aromatization involving indolinium ion intermediate. A wide range of 3-functionalized indoles have been synthesized. The method is employed for the synthesis of 3,3?-bis-indoles and a dimeric 3-indole derivative. Moreover, this protocol is used to obtain naturally occuring amino acid tryptamine.