Synthesis of Multisubstituted Arylnitriles via Tf₂O-Mediated Benzannulation of Enaminones with Acylacetonitriles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

A novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 1] benzannulation enaminones acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation aromatization. Additionally, trifluoromethanesulfonate 6 identified as crucial intermediate in this process.

Язык: Английский

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Switchable Synthesis of Spirodihydroindolizines and Indolizines from Aurones and Pyridin-2-yl Active Methylene Compounds

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1753 - 1761

Опубликована: Янв. 22, 2024

A novel and flexible domino reaction of aurones with pyridin-2-yl active methylene compounds promoted by I2/BF3 has been developed to afford spirodihydroindolizines indolizines in a controllable manner. When the was performed 1,2-dichloroethane at 80 °C, variety were obtained, whereas it almost exclusively provided series when mixed solvent N,N-dimethylformamide relatively higher temperature 100 °C. Being metal-free, excellent product selectivity, high atom economy, good functional group tolerance, feasibility for large-scale synthesis are salient features methodology.

Язык: Английский

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The most Recent Compilation of Reactions of Enaminone Derivatives with various Amine Derivatives to Generate Biologically Active Compounds

Mini-Reviews in Medicinal Chemistry, Год журнала: 2023, Номер 24(8), С. 793 - 843

Опубликована: Сен. 14, 2023

Heterocyclic derivatives serve as the fundamental components of both natural and synthetic drugs. Enaminones play a crucial role foundational units in synthesis numerous bioactive heterocyclic compounds, including pyrazoles, pyridines, oxazoles, isoxazoles, well fused structures like indoles, carbazoles, quinolines, acridines, phenanthridines. These diverse rings are well-known for their various therapeutic activities, encompassing anticancer, anti-inflammatory, antimicrobial, antidepressant, antiviral properties. By reacting with nitrogenbased nucleophiles, enaminones can generate azoles, azines, systems. This study focuses on recent advancements enaminone reactions (a) nitrogen-based such aliphatic amines, aniline, hydroxylamine, hydrazine derivatives, guanidine urea, thiourea (b) electrophiles, diazonium salts. have led to wide range compounds from 2010 end 2022.

Язык: Английский

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Cu(II)‐Catalyzed [3+2]‐Annulation of 2‐Pyridinyl‐substituted p‐Quinone Methides with Enaminones: Access to Functionalized Indolizine Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(19), С. 3271 - 3276

Опубликована: Авг. 17, 2023

Abstract This article describes an effective and atom‐economical protocol to access a wide range of synthetically important functionalized indolizine derivatives. transformation basically takes place through Cu(II) catalyzed formal [3+2] annulation 2‐pyridinyl substituted p ‐quinone methides with enaminones. method displayed good functional group tolerance and, was found be for most the enaminones ‐QMs, corresponding indolizines were obtained in moderate yields.

Язык: Английский

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Synthesis of Highly Functionalized Indolizines via NIS-Promoted Spiroannulation/Ring-Opening Aromatization of Alkylidene Oxindoles with 2-(Pyridin-2-yl)acetate Derivatives

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

A novel NIS-promoted domino reaction of alkylidene oxindoles with 2-(pyridin-2-yl)acetate derivatives has been established, enabling the efficient and straightforward synthesis a vast variety highly functionalized indolizines via sequential spiroannulation ring-opening aromatization processes. The protocol features mild conditions, broad substrate scope, high efficiency, scalability, applicability for preparation CF3-containing indolizines. Furthermore, functional groups in indolizine framework provide feasibility follow-up derivatization. Based on mechanistic studies, plausible radical mechanism is proposed to elucidate formation

Язык: Английский

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Chiral Phosphoric Acid-Catalyzed Asymmetric Friedel–Crafts Addition of Indolizine to Cyclic N-Sulfonyl Imine

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14676 - 14687

Опубликована: Окт. 3, 2023

A highly efficient chiral phosphoric acid-catalyzed enantioselective Friedel-Crafts addition of indolizine to cyclic N-sulfonyl imine has been established. The newly developed protocol, which probably proceeds via a monoactivation reaction pathway, allows the access enantioenriched sulfonamide functionalized indolizines with excellent yields (up 99%) and enantioselectivities 99%). Moreover, synthetic utility this protocol explored some chemical transformations.

Язык: Английский

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Synthesis of α/β-Aromatic Peroxy Thiols Mediated by Iodine Source

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3049 - 3057

Опубликована: Фев. 9, 2024

Peroxygenated compounds have wide applications in various fields, including chemistry, pharmaceutical medicine, and materials science. However, there is still a need for more efficient environmentally friendly synthesis methods such compounds. Herein, we investigated the two-step, one-pot, regioselective of α/β-aromatic peroxy thiols. We explored substrates solvents reaction identified optimal conditions. successfully obtained several thiols moderate to good yields via selective generation effective intermediates iodoalkyl peroxides at room temperature without metal catalysts.

Язык: Английский

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Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes

Molecules, Год журнала: 2024, Номер 29(9), С. 2061 - 2061

Опубликована: Апрель 29, 2024

Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This involved formation C–N C–C bonds compounds with stereoselectivity excellent functional group tolerance.

Язык: Английский

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A pyridine-boryl radical mediated cascade reaction towards the synthesis of indolizines: a computational mechanistic analysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4168 - 4175

Опубликована: Янв. 1, 2024

Computational analysis reveals a boryl-radical-enabled cross-coupling pathway for synthesizing indolizines, emphasizing the role of H-shuttles in facilitating reactions.

Язык: Английский

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Exploring the decadal evolution of indolizine scaffold for anticancer innovations: a comprehensive analysis

Medicinal Chemistry Research, Год журнала: 2024, Номер 33(9), С. 1491 - 1510

Опубликована: Июль 25, 2024

Язык: Английский

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