Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides <i>via</i> palladium-catalyzed intramolecular cyclization

Shên, Hui; Du, Yu; Kan, Jian; Su, Weiping

doi:10.1039/d2ob00480a

Cited by 5 publications

(4 citation statements)

References 109 publications

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“…13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ = 180.3, 141.7, 129.6, 127.8, 124.1, 122.3, 109.6, 47.1, 29.7, 23.6 ppm. [23] Following the general procedure D, the title compound was isolated as a pale-yellow oil eluting with 5 % ethyl acetate in hexane (34 mg, 78 %). 1 H NMR (500 MHz, CDCl 3 ): δ = 7.31-7.26 (dd, J = 18.4, 7.6 Hz, 2H), 7.09-7.06 (t, J = 7.5 Hz, 1H), 6.84 (d, J = 7.8 Hz, 1H), 3.43 (t, J = 5.8 Hz, 1H), 3.22 (s, 3H), 2.07-1.99 (m, 2H), 0.93-0.90 ppm (t, J = 7.4 Hz, 3H).…”

Section: -Hexylindolin-2-onementioning

confidence: 99%

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Ghosh

Banerjee

2023

ChemCatChem

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Herein, a simple and efficient nickel-catalyzed C-3-selective alkylation of 2-oxindoles using primary alkyl and allylic alcohols have been demonstrated. The catalytic protocol enables transformations in the presence of free hydroxyl group, amine, cycloalkanes, olefins, and lactam including more challenging C2-C4 alcohols, citronellol and oleic acid derived alcohol in up to 96 % yield. Initial mechanistic studies and deuterium labelling experiments were performed. Synthetic modulations of the lactam enabled new routes for the synthesis of C-3-substituted indoles, indolines, and un-symmetric urea derivatives.

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Section: -Hexylindolin-2-onementioning

confidence: 99%

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Ghosh

Banerjee

2023

ChemCatChem

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“…A method for the synthesis of 3-substituted 2-oxindoles has been developed by Su and colleagues. [68] The 2-bromo-Nphenylpropanamide starting materials were easily available and their intramolecular cyclization catalyzed by Pd(OAc) 2 and L18 ligand showed good functional group tolerance. Scheme 42 indicates a broad substrate scope and medium to excellent product yields.…”

Section: Intramolecular Ring Formationsmentioning

confidence: 99%

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Molnár

2023

ChemistrySelect

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This review aims to collect and analyze recent results with respect to the use of varied palladium preparations in the synthesis of five-membered nitrogen heterocycles including condensed derivatives. Results have been selected with focus on studies of the last three years. Furthermore, a common feature of all methods treated here is that the nitrogencontaining five-membered ring is formed via ring closing of appropriate starting materials. Selected examples discussed will reveal that a plethora of products from small monocycles to condensed multi-ring systems can be successfully accessed. Major features are wide product ranges, high product yields and stereoselectivities often achieved under mild reaction conditions.

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“…The authors have cited additional references within the Supporting Information. [47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62] 100010434), fellowship code LCF/BQ/PI18/11630023. R. A. and J. R. C.-A.…”

Section: General Procedures For Materials Preparationmentioning

confidence: 99%

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

2023

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An efficient heterogeneous silver‐catalyzed α‐alkylation of nitriles and oxindoles using alcohols via borrowing hydrogen strategy has been developed for the first time. The active nanostructured material, namely [Ag/Mg4Al‐LDH], composed by silver nanoparticles (3‐4 nm average particle size) homogeneously stabilized onto a [Mg4Al‐LDH] support with suitable Brönsted basic properties, constitutes a stable catalyst for the sustainable building of novel C‐C bonds from alcohols and C‐nucleophiles. By applying this catalyst, a broad range of α‐functionalized nitriles and oxindoles has been accessed with good to excellent isolated yields and without the addition of external bases. Moreover, the novel silver nanocatalyst has also demonstrated its successful application to the cyclization of N‐[2‐(hydroxymethyl)phenyl]‐2‐phenylacetamides to afford 3‐arylquinolin‐2(1H)‐ones, through a one‐pot dehydrogenation and intramolecular α‐alkylation. Control experiments, kinetic studies and characterization data of a variety of [Ag/LDH]‐type materials confirmed the silver role in the dehydrogenation and hydrogenation steps, while [Mg4Al‐LDH] matrix is able to catalyze condensation. Interestingly, these studies suggest as key point for the successful activity of [Ag/Mg4Al‐LDH], in comparison with other [Ag/LDH]‐type nanocatalysts, the suitable acid‐base properties of this material.

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Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides via palladium-catalyzed intramolecular cyclization

Abstract: In contrast to aromatic halides, coupling reactions involving oxidative addition of alkyl halides to transition metal tend to be more challenge, especially secondary or tertiary halides. Herein a palladium-catalyzed intramolecular...

Cited by 5 publications

References 109 publications

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

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Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides via palladium-catalyzed intramolecular cyclization

Abstract: In contrast to aromatic halides, coupling reactions involving oxidative addition of alkyl halides to transition metal tend to be more challenge, especially secondary or tertiary halides. Herein a palladium-catalyzed intramolecular...

Cited by 5 publications

References 109 publications

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Nickel Catalyzed Alkylation of Oxindoles with Alkyl Alcohols

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Silver Supported Nanoparticles on [Mg4Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

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About

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols