Recent Advances in Multicomponent Electro‐Organic (Electrochemical) Synthesis of Heterocycles

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июль 20, 2023

Abstract In terms of pharmaceuticals and biological applications, synthesis complex organic molecules is a significant fast‐developing area. this context, electrosynthesis an alternative way to the traditional methods for chemo‐, regio‐, stereoselective syntheses. Electro‐organic reactions occur at room temperature normal pressure, through transferring electrons. It has been found that mild approach preparing electrophilic substrates, bases, nucleophiles in situ , from highly stable low‐level reagents; which can be further applied make heterocycles more accessible. While several promising exist, multi‐component (MCRs) have drawn much attention both academia industry worldwide, since they are cost‐efficient environmentally friendly. Combining MCRs produced great strategy field research. This review focuses on recent advances electrochemical heterocyclic compounds via reactions, reported between 2015 March 2023.

Язык: Английский

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Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7227 - 7232

Опубликована: Авг. 20, 2024

We present an electrochemical alkylation of azauracils using N-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several are shown to undergo with array NHPI esters (1°, 2°, 3°, sterically congested), providing the desired products in good excellent yields. This operationally simple method is robust, scalable, suitable for both batch flow setups.

Язык: Английский

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Recent Advances in Electrochemical Cascade Cyclization Reactions

Synthesis, Год журнала: 2023, Номер 55(18), С. 2911 - 2925

Опубликована: Фев. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Язык: Английский

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Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

Advanced Materials, Год журнала: 2023, Номер 35(49)

Опубликована: Март 25, 2023

Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses largely relied on multistep approaches or the conventional Scholl reaction. However, reactions are inefficient with electron-deficient substrates, require stoichiometric chemical oxidants, typically occur presence strong acid. In sharp contrast, electrochemistry has gained considerable momentum during past decade an alternative for facile straightforward assembly, generally via electro-oxidative dehydrogenative annulation, releasing molecular hydrogen sole byproduct by evolution This review provides overview recent significant advances field electrochemical various until January 2023.

Язык: Английский

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Electrochemical Regioselective Sulfenylation of 2H-Indazoles with Thiols in Batch and Continuous Flow

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 13845 - 13855

Опубликована: Окт. 12, 2022

A novel electrochemical cross-dehydrogenative C-S bond coupling of aryl thiols with 2H-indazole is reported. Thiol-functionalized 2H-indazoles were synthesized under catalyst-, oxidant-, and metal-free conditions innocuous hydrogen as the sole byproduct at ambient temperature. Furthermore, continuous flow using a graphite/Ni cell used to obtained 3-(arylthio)-2H-indazole compounds on gram scale within residence time 39 min. Detailed mechanistic studies including control experiments cyclic voltammetry are provided support radical-radical cross-coupling pathway.

Язык: Английский

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Synthetic Strategies for the Construction of Indolizines and Indolizine‐fused Compounds: Thienoindolizines and Indolizinoindoles

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(10)

Опубликована: Авг. 22, 2023

Abstract This paper provides a review on various methodologies developed for the synthesis of different indolizine derivatives and an overview their application. These include thienoindolizine indolizino[8,7‐ b ]indole derivatives. The nucleus occurs as privileged scaffold many natural synthetic molecules with significant biological activity. Fused‐indolizines such thienoindolizines indolizinoindole are great interest, due to antitumor, antimicrobial enzyme inhibitor Because widespread use in chemical, medicinal, biological, materials science research, indolizines fused attractive targets search efficient methods construction.

Язык: Английский

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Electrochemical cascade reactions: an account of recent developments for this modern strategic tool in the arsenal of chemical synthesis

Green Chemistry, Год журнала: 2023, Номер 25(24), С. 10144 - 10181

Опубликована: Янв. 1, 2023

The electrochemical cascade process majorly satisfies the essential criteria of green synthesis. Being an Integrated synthetic strategy it can produce more molecules in a shorter time and thus provides modern strategic tool arsenal chemists.

Язык: Английский

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Electrochemical Post-Ugi Cyclization for the Synthesis of Highly Functionalized Spirolactams

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13977 - 13994

Опубликована: Сен. 11, 2023

The combination of the Ugi reaction and electro-organic synthesis can aid in creation novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from has developed, which produce C–S, C–Se, C–C═O functionalized five-membered spirolactams mediated by electricity under catalyst- metal-free conditions. Notably, approach be applied using microelectro-flow reactor (μ-EFR) for gram-scale synthesis. described synthesize complex azaspiro-fused tricyclic scaffolds with high diastereo- regioselectivity, highlighting its versatility potential.

Язык: Английский

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Electrochemical Annulation of p-Alkoxy or p-Hydroxy Anilines with Enaminones for Selective Indole and Benzofuran Synthesis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

The green and sustainable electrochemical oxidative cyclization of enaminones with p-methoxy/p-hydroxy anilines has been developed, enabling the regioselective synthesis indoles benzofurans. methods are significant advantage not only due to mild metal-free conditions, but also because employment easily available stable aniline substrates replace unstable quinoneimide for a similar annulation in previous work.

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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