Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(15), С. 11023 - 11035

Опубликована: Июль 21, 2023

Herein, a divergent and selective synthesis of (E)-3-alkylidene oxindole, which is highly valuable framework due to its presence in biologically important molecules, via palladium-catalyzed multicomponent reaction 3-diazo isocyanide, aniline has been developed. Further, the feasibility was demonstrated by employing differently substituted oxindoles, isocyanides, anilines as starting material obtaining corresponding products 31-83% isolated yields. Besides, plausible mechanism presented further investigated using DFT calculations suggest formation Pd-carbene complex ketenimine intermediate key step during catalytic cycle.

Язык: Английский

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Palladium-catalyzed cyclization/carbonylation of iodoarene-tethered propargyl ethers with nitroarenes for the synthesis of acetamides-functionalized benzofurans

Journal of Catalysis, Год журнала: 2023, Номер 428, С. 115166 - 115166

Опубликована: Окт. 13, 2023

Язык: Английский

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Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C–C Cleavage of Cyclobutanols

Organometallics, Год журнала: 2022, Номер 41(5), С. 649 - 658

Опубликована: Март 3, 2022

We report a Pd-catalyzed route to heterocycles bearing tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by C-C cleavage cyclobutanol derivatives. An alkenyl-Pd(II) intermediate has been isolated and characterized X-ray diffraction studies. Interestingly, nature tethering alkynyl chain influences E/Z stereochemistry alkenyl fragment in functionalized heterocycles.

Язык: Английский

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Binaphthyl-Stabilized Palladium Nanoparticle-Catalyzed Stereoselective Synthesis of 3-Arylidene-2-oxindoles via One-Pot Heck-like Carbocyclization/Nucleophilic Addition

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1730 - 1741

Опубликована: Янв. 24, 2023

Stereoselective, one-pot synthesis of 3-arylidene-2-oxindoles has been accomplished via Heck-like carbocyclization/nucleophilic addition N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide, phenylacetylene, and secondary amine using binaphthyl stabilized palladium nanoparticles (Pd-BNP) as a reusable catalyst. Less reactive aryl bromides generally provided similar yield compared with more iodides. The Pd-BNP nanocatalyst recovered recycled for five catalytic cycles only an insignificant reduction in particle size, reactivity, reaction yield.

Язык: Английский

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Green nanoparticles for stereospecific and stereoselective organic synthesis

Elsevier eBooks, Год журнала: 2023, Номер unknown, С. 195 - 240

Опубликована: Янв. 1, 2023

Язык: Английский

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Consecutive multicomponent syntheses of N-substituted 3-arylallylidene indolones – Solid-state emitters and photoisomerization

Dyes and Pigments, Год журнала: 2021, Номер 198, С. 109938 - 109938

Опубликована: Ноя. 13, 2021

Язык: Английский

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A Scalable Total Synthesis of Deoxyrhapontigenin from Low-Cost α-Resorcylic Acid

Journal of the Brazilian Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A scalable total synthesis for deoxyrhapontigenin (DRG) was successfully accomplished using low-cost α-resorcylic acid as a starting material. Our approach initiates with the protection of phenolic groups methoxymethyl, resulting in derivative expensive 3,5-hydroxybenzaldehyde, critical component Wittig and Perkin approaches stilbenoid synthesis. Additionally, corresponding olefin Heck reaction formal resveratrol were produced over 85% yield. The seven steps from initial carboxylic acid, yielding product an average purity higher than 98%, confirmed by quantitative nuclear magnetic resonance (NMR) analysis.

Язык: Английский

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Stereoselective Construction of 3-(Aminoalkylidene)oxindoles in One Pot: Development of a Novel, Robust, and Scalable Process for the Multigram-Scale Preparation of Nintedanib

Organic Process Research & Development, Год журнала: 2024, Номер 28(3), С. 754 - 769

Опубликована: Фев. 16, 2024

A palladium-catalyzed novel stereoselective Heck/Buchwald–Hartwig cascade reaction of substituted N-(2-iodophenyl)propiolamides and amines has been established to furnish a series 3-(aminoalkylidene)oxindole scaffolds with good yields. In addition, we report the development robust, scalable, convergence approach leading synthesis nintedanib (1). Salient features include production key oxindole intermediate 17 via our advanced cascade, which enables reduction number synthetic steps. Moreover, avoids expensive column chromatography purification method for all Further, also disclosed an alternative route toward another kinase inhibitor hesperadin (2) following above-mentioned method.

Язык: Английский

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Pd-catalyzed 5-exo-dig cyclization/etherification cascade of N-propargyl arylamines for the synthesis of polysubstituted furans

Chemical Communications, Год журнала: 2024, Номер 60(60), С. 7721 - 7724

Опубликована: Янв. 1, 2024

A method for the synthesis of furans bearing indoline skeletons was developed

Язык: Английский

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Ruthenium-catalyzed Heck coupling of 3-arylidene-oxindoles with alkenes: a facile synthesis of 3-allylidene-2(3H)-oxindoles

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A simple and efficient Ru(ii)-catalyzed olefination of 3-(arylbenzylidene)indolin-2-ones with alkenes is described. This protocol found to be tolerant a wide range functional groups affords various products in good yields.

Язык: Английский

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