7135-32-2Relevant articles and documents
A New Radical Based Synthesis of Lactams and Indolones from Dithiocarbonates (Xanthates).
Axon, Jonathan,Boiteau, Laurent,Boivin, Jean,Forbes, Judith E.,Zard, Samir Z.
, p. 1719 - 1722 (1994)
N,N-disubstituted α-(xanthyl)-acetamides with an olefin on one of the substituents undergo cyclisation to a lactam by a radical chain reaction involving transfer of the xanthate group; anilides lead to the corresponding indolones.
Copper(I) reactions in N-heterocycle synthesis: Efficient preparation of substituted pyrrolidinones
Davies, David T.,Kapur, Neha,Parsons, Andrew F.
, p. 8615 - 8618 (1999)
Reaction of halo-enamides with copper(I) chloride in boiling toluene has been shown to produce unsaturated pyrrolidinones in excellent yield (81-94%). Both di- and trichloroamide precursors can be used to form dienes via an initial 5-endo-trig radical cyc
New cell cycle checkpoint pathways regulators with 2-Oxo-indoline scaffold as potential anticancer agents: Design, synthesis, biological activities and in silico studies
Abd El-wahab, Hend A. A.,Aboul-Fadl, Tarek,Ali, Ahmed M.,El-Awady, Raafat,Mansour, Hany S.
, (2022/01/31)
3-Arylidene-2-oxo-indoline derivatives are at the heart of a wide range of clinically, medicinally and biologically important compounds among the 2-oxo-indolines. A number of 3-arylidene-2-oxo-indolines have been approved for clinical application. Accordi
Heterogeneous palladium-catalysed intramolecular C(sp3)[sbnd]H α-arylation for the green synthesis of oxindoles
Anastasiou, Ioannis,Chen, Shaomin,Ferlin, Francesco,Gu, Yanglong,Liu, Ping,Minio, Francesco,Salameh, Nihad,Santoro, Stefano,Vaccaro, Luigi
, (2022/03/27)
Herein, we present our results on the development of a waste-minimized protocol for the synthesis of oxindoles using cyclopentyl methyl ether (CPME) as a safe and green reaction medium and palladium on carbon (Pd/C) as a reusable catalyst. This protocol is efficiently applied to a variety of substrates affording products with excellent yields, minimal metal contamination and minimum waste production. The catalyst was recovered and reused for four consecutive runs without any apparent loss of efficiency. Moreover, products were isolated by simple precipitation from heptane with no need for chromatographic separations, and both CPME and heptane were recovered. Waste-minimization is reflected by the low E-factor calculated for the presented protocol.
A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids
Huang, Tiao,Kong, Dulin,Li, Yue,Liu, Li,Wu, Mingshu
, p. 2321 - 2328 (2021/09/22)
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.
3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom
Zhao, Hongcai,Zhang, Zhengbing,Lu, Wenhua,Han, Pan,Wang, Wei,Jing, Linhai
supporting information, (2021/10/01)
A simple and efficient strategy has been established for the synthesis of δ-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and α,β-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.
Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide
Zhao, Guodong,Liang, Lixin,Wang, Eryu,Lou, Shaoyan,Qi, Rui,Tong, Rongbiao
supporting information, p. 2300 - 2307 (2021/04/12)
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.
Green method for preparing oxindole derivative
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Paragraph 0033-0035, (2021/06/26)
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.
Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles
Gandhi, Thirumanavelan,Nagaraja, C. M.,Panyam, Pradeep Kumar Reddy,Rajeshwaran, Purushothaman,Sreedharan, Ramdas,Yadav, Saurabh
supporting information, p. 3843 - 3847 (2020/06/03)
Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.
Preparation method of optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde
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Paragraph 0138-0140; 0142-0143, (2020/10/05)
The invention discloses a preparation method of optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde. The preparation method comprises the following steps: adding vinyl oxoindole spiro-cyclopropane and olefine aldehyde as raw materials into a solvent, respectively adding secondary amine, palladium salt, a ligand and an additive, stirring the mixture at room temperature, then removing the solvent, and purifying by virtue of a rapid column chromatography, so as to obtain the optically active 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde. The 2-aryl spiro [cyclopentane-1, 3'-indole]-3-formaldehyde prepared by the method has the characteristics of mild reaction conditions, simple process, controllable optical activity, high yield and the like.
