Spirooxindoles: Recent report of green synthesis approach

Green Synthesis and Catalysis, Год журнала: 2023, Номер 5(1), С. 1 - 13

Опубликована: Авг. 15, 2023

Spirooxindole is a compound with unique framework and broad bioactivities in medicine. In this study, we have reviewed various approaches or methods synthesizing spirooxindole derivatives focused on green synthesis. Synthesis of spirooxindoles mainly carried out through multicomponent reactions combined such as the use heterogeneous catalysts (nano-sized, magnetic, metal-complex, metal-organic catalysts), deep eutectic solvent, solvent-free reactions, catalyst-free well ultrasonic microwaves irradiation. The method addition to obtaining high yields, it also offers reductions hazardous chemicals, energy use, purification processes, waste generation. As result, synthesis are more environmentally friendly.

Язык: Английский

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Pd-catalyzed exclusively regioselective [5 + 4] cycloaddition for the construction of 1,5-di/ox-azonanes

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1680 - 1685

Опубликована: Янв. 1, 2023

An efficient approach for the exclusively regioselective construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed.

Язык: Английский

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Enantioselective Construction of Vicinal Quaternary-Tetrasubstituted Carbon Stereocenters by Copper-Catalyzed Decarboxylative Propargylic Substitution

Organic Letters, Год журнала: 2022, Номер 24(41), С. 7671 - 7676

Опубликована: Окт. 13, 2022

Enantioselective construction of vicinal tetrasubstituted carbon stereocenters is a formidable challenge in organic synthesis. A copper-catalyzed asymmetric decarboxylative propargylic substitution with 3-amino oxindoles as trisubstituted nucleophiles and cyclic carbonates tertiary electrophiles was developed. range 3-amino-3,3′-disubstituted bearing quaternary-tetrasubstituted were obtained high yields good to excellent stereoselectivities (up 98% yield, >20:1 dr, 98.5:1.5 er).

Язык: Английский

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Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh₃ Dual Catalysis

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9186 - 9190

Опубликована: Дек. 15, 2023

The photoredox/PPh3-mediated cyclization of 2-isocyanobiaryls has been developed. A substantial range functional-group-rich phenanthridine derivatives were synthesized at room temperature in a highly selective and atom-economic manner. Mechanistic studies suggested that the process is probably mediated both by Ph3P radical cation with key 1,2-hydride transfer hydrogen atom generated through O–H bond homolytic cleavage Ph3P–OH intermediate.

Язык: Английский

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Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction

Chemical Communications, Год журнала: 2023, Номер 59(21), С. 3107 - 3110

Опубликована: Янв. 1, 2023

The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence a carbenoid intermediate, this protocol represents first non-carbenoid variant Doyle-Kirmse reaction. Under mild conditions, variety tertiary thioethers have readily prepared in good excellent yields.

Язык: Английский

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Synthesis of Sulfone Methylene-Substituted Indolines by Radical Cascade Cyclization of 2-Alkynylaniline Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10678 - 10683

Опубликована: Июль 16, 2024

A radical cascade cyclization of 2-alkynylaniline derivatives with sulfonyl chlorides was developed to construct C3-sulfone methylene-substituted indolines in yields 21 85% a broad substrate scope under metal- and base-free conditions. This protocol could simultaneously build three new chemical bonds employ solvent-radical relay strategy, providing rapid concise approach toward an indoline framework. Scale-up reactions this method further transformations afford useful were also demonstrated.

Язык: Английский

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Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(3), С. 258 - 262

Опубликована: Май 10, 2022

The first diastereodivergent formal [4 ​+ ​1] cycloaddition reactions of azoalkenes with p-quinone methides (p-QMs) have been accomplished. reported reaction occurred via a domino oxa-1,4-addition/1,6-addition process, allowing the use common as C1 synthons. A broad range 2,3-dihydrobenzofurans was smoothly prepared in good yields and reversible diastereoselectivities. steric hindrance hydrogen-bonding interaction were proposed to account for two different modes diastereo-control. projected features employment azoalkene carbene-like synthon, mild conditions, substrate scope tunable diastereoselectivity.

Язык: Английский

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Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Molecules, Год журнала: 2022, Номер 27(19), С. 6708 - 6708

Опубликована: Окт. 9, 2022

Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines hydrazones) under a variety of conditions, both react with wide range substrates many kinds reactions. Most these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand aza-Diels–Alder This review focuses on the reports during last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, 1,4-diaza-1,3-butadienes intermediates to synthesize heterocycles such indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, imidazolidine, among others. Fused heterocycles, quinazoline, isoquinoline, dihydroquinoxaline derivatives, are also included review.

Язык: Английский

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Rhodium(III)-Catalyzed Annulation Synthesis of Difluorinated Quinazolinone Derivatives Using an Amide Carbonyl as the Directing Group

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9627 - 9640

Опубликована: Июнь 18, 2024

The use of amide carbonyl groups substrates as weakly coordinating directing has received a significant amount attention. Recently, difluoromethylene alkynes have been successfully used in fluorination reactions, resulting the preparation various fluorine-containing compounds. This work describes [4+2] annulation method for creating range fluorinated quinolino[2,1-

Язык: Английский

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3-Phenacylideneoxindoles in organic synthesis: Recent developments

Tetrahedron Letters, Год журнала: 2023, Номер 129, С. 154725 - 154725

Опубликована: Авг. 29, 2023

Язык: Английский

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