3335-98-6Relevant articles and documents
The first Pummerer cyclisations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin
McAllister, Laura A.,Brand, Stephen,De Gentile, Remy,Procter, David J.
, p. 2380 - 2381 (2003)
α-Sulfanyl N-aryl acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclisation upon activation of the sulfur link, to give oxindoles; heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide.
Copper-catalyzed N-arylation of oxindoles
Phillips, Dean P.,Hudson, Andrew R.,Nguyen, Bao,Lau, Thomas L.,McNeill, Matthew H.,Dalgard, Jackline E.,Chen, Jyun-Hung,Penuliar, Richard J.,Miller, Todd A.,Zhi, Lin
, p. 7137 - 7138 (2006)
The coupling of aryl bromides or iodides with oxindoles using a copper iodide-N,N′-dimethylethylene diamine system is presented. The reaction proceeds efficiently and tolerates a variety of substitution patterns.
Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst
Phan Thi Thanh, Nga,Dang Thi Thu, Huong,Tone, Masaya,Inoue, Hayato,Iwasa, Seiji
, (2020/10/02)
This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).
Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively
Xiong, Cheng,Cheng, Kunpeng,Wang, Jiahua,Yang, Fulai,Lu, Jinrong,Zhou, Qingfa
, p. 9386 - 9395 (2020/08/14)
A novel method of iodine-catalyzed aerobic oxidation with spirovinylcyclopropyl oxindoles under mild conditions has been described. A series of spiro-1,2-dioxolanes were prepared in good to excellent yields and considerable diastereoselectivities. The new approach is operationally simple, scalable, and tolerant of various functional groups.
PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles
Li, Gen,Luzung, Michael R.,Nykaza, Trevor V.,Radosevich, Alexander T.,Yang, Junyu
supporting information, p. 4505 - 4510 (2020/02/05)
An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C?N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.
Preparation method for N-phenyl indolone
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, (2018/09/21)
The invention especially relates to a preparation method for N-phenyl indolone, belonging to the field of organic synthesis. The preparation method for N-phenyl indolone comprises the following steps:subjecting diphenylamine (a compound as shown in a formula II) and chloroacetyl chloride (a compound as shown in a formula III) to a condensation reaction to prepare 2-chloro-N,N-diphenylacetamide (acompound as shown in a formula IV); subjecting 2-chloro-N,N-diphenylacetamide and acetate to an esterification reaction so as to obtain 2-acetoxy-N,N-diphenylacetamide (a compound as shown in a formula V); and subjecting 2-acetoxy-N,N-diphenylacetamide to a ring closure reaction so as to obtain N-phenyl indolone. The preparation method provided by the invention is a clean high-efficiency synthesis method for N-phenyl indolone; in the whole preparation process, high-contamination raw materials are discarded, and reaction temperature is lowered; and the method is friendly to environment and safe and simple to operate, and has great industrial application value.
Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde
Zhao, Jian-bo,Ren, Xinfeng,Zheng, Bu-quan,Ji, Jian,Qiu, Zi-bin,Li, Ya
supporting information, p. 44 - 51 (2018/10/02)
Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.
Method for synthesizing indole-2-ketone compound
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Paragraph 0058; 0060, (2018/11/03)
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for synthesizing an indole-2-ketone compound. Indole-2-ketone compound synthesis is difficultly industrialized due to the problems of poor yield, cost and environmental protection in the prior art, the method includes the steps: taking a compound X as a catalyst in a hydrous organic solvent; performing reaction on indole and water under the condition of oxidizing agents to obtain the indole-2-ketone compound. The compound X is preferably iodine, and the indole-2-ketone compound is applicable to the field of organic synthesis and medicine.
Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation
Jiang, Xinpeng,Zheng, Cong,Lei, Lijun,Lin, Kai,Yu, Chuanming
, p. 1437 - 1442 (2018/04/06)
A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.
Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition
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Paragraph 0034-0035, (2018/07/06)
The invention relates to a method for directly synthesizing substituted 2-indolone by substituted indole under the neutral condition. The method comprises the following steps of sequentially adding organic solvents and water according to the proportion of 1:1-1:20 at the room temperature; then, adding high-iodine reagents; raising the temperature to 40 to 160 DEG C; then, adding indole; performingreaction for 1 to 8 hours to obtain the substituted 2-indolone compounds. The method has the main innovation point that under the neutral condition, substituted 2-indolone is directly synthesized through indole oxidization; the use of strong acid reagents is avoided. The method has the advantages that the raw materials are cheap and can be easily obtained; the operation is simple and convenient;the substrate universality is high; the reaction yield is high, and the like.
