Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF₃-ynones via C–H/N–H/C–N/C–C bond cleavage

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Language: Английский

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Recent Advances in Electrochemical Cascade Cyclization Reactions

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2911 - 2925

Published: Feb. 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

Language: Английский

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Synthesis and Application of Well‐Defined Fluoroalkyl Zinc Complexes

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 17, 2024

Abstract Fluoroalkyl groups play an irreplaceable role in the field of pharmaceutical and agrochemical industry due to their unique properties. Based on this, it is crucial effectively introduce fluoroalkyl into target molecules. In this review, we describe synthesis well‐defined zinc complexes applications fluoroalkylation compounds. Different from reactivities copper complexes, often needed be combined with or nickel catalysts when participating reactions. From perspective reaction mechanism, transfer trifluoromethyl formed highly active reagents, which can directly used for fluoroalkylation. most cases, desired products were provided excellent yields.

Language: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Synthesis of Hypervalent Iodine Diazo Compounds and Their Application in Organic Synthesis

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(5)

Published: Oct. 17, 2023

Diazomethyl-substituted iodine(III) compounds with electron-withdrawing groups (EWG) connected to diazo methyl center were a type of donor-acceptor potential reaction abilities similar ordinary compounds. Although several diazomethyl-substituted synthesized and used in the nucleophilic substitution reactions as early 1994, synthesis application new have only been reported certain extent recent years. In presence rhodium catalyst, photocatalyst, or nucleophiles, can be converted into rhodium-carbenes, diazomethyl radicals, ester radicals intermediates, which key intermediates for formation chemical bonds. The aim this review is give an overview organic synthesis.

Language: Английский

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Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(11)

Published: Dec. 7, 2023

Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances bioactivity by altering pharmacological profile molecule. Trifluoromethyl-β-dicarbonyls have emerged as pivotal building blocks synthetic due to their facile accessibility, stability and remarkable versatility. Owing presence nucleophilic electrophilic sites, they offer multifunctional sites for reaction. This review covers meticulous exploration multifaceted role, encompassing an in-depth analysis mechanism, extensive scope, limitations wide-ranging applications diverse synthesis, covering literature from 21

Language: Английский

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Acid-Switchable Synthesis of Trifluoromethylated Triazoles and Isoxazoles via Reaction of CF3-Ynones with NaN3: DFT Study of the Reaction Mechanism

International Journal of Molecular Sciences, Journal Year: 2022, Volume and Issue: 23(23), P. 14522 - 14522

Published: Nov. 22, 2022

A detailed study of the reaction CF3-ynones with NaN3 was performed. It found that permits selective synthesis either 4-trifluoroacetyltriazoles or 5-CF3-isoxazoles. The chemoselectivity switchable via acid catalysis. in EtOH produced high yields 4-trifluoroacetyltriazoles. In contrast, formation 5-CF3-isoxazoles observed under catalysis by acids. This acid-switchable procedure can be performed at sub-gram scale. possible mechanism supported DFT calculations. synthetic utility prepared demonstrated.

Language: Английский

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The cyclization/rearrangement of α-hydroxy ketones with trifluoromethyl N-acylhydrazones to synthesize multi-substituted trifluoromethyloxazolines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(96), P. 14293 - 14296

Published: Jan. 1, 2023

A highly efficient and metal-free [3+2] cyclization/rearrangement reaction toward the synthesis of multisubstituted trifluoromethyloxazolines from α-hydroxyketones trifluoromethyl N-acylhydrazones has been developed. The unprecedented rearrangement amide fragment under acidic conditions after cleavage N-N bond acylhydrazones opened up new avenues for development reactions involving N-acylhydrazones. DFT calculations show that mechanism involves multiple proton transfer processes.

Language: Английский

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Application of Aromatic Substituted 2,2,2-Trifluoro Diazoethanes in Organic Reactions

Current Organic Chemistry, Journal Year: 2022, Volume and Issue: 26(7), P. 639 - 650

Published: April 1, 2022

Abstract: This review provides an overview of metal-, nonmetal-, light-, or catalyst free-promoting reactions aromatic substituted 2,2,2-trifluoro diazoethanes with organic molecules for the synthesis trifluoromethyl-substituted compounds. Several approaches will be reviewed and divided into (i) copper-, iron-, Trop(BF4)-, B(C6F5)3-, rhodium-promoted silanes, amines, mercaptans, phosphonates, p-cyanophenol, benzoic acid, diphenylphosphinic boranes nBu3SnH, (ii) rhodium-catalyzed amides phenylhydroxylamine, (iii) rhodium-, silver-, light-catalyzed alkynes, (iv) palladium-, rhodium- iron-catalyzed alkenes, (v) BF3·OEt2-, tin- TBAB-catalyzed HF·Py, (difluoroiodo)toluene (p-TolIF2), TMSCF3, AgSCF3, TMSCF2Br 1,3-dicarbonyl compounds, (vi) gold/silver- indoles, benzene compounds pyridines, (vii) palladium-catalyzed reaction benzyl allyl bromides.

Language: Английский

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Synthesis of trifluoromethyl substituted heterocyclic compounds with β-trifluoromethylated acrylates

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(20), P. 1707 - 1724

Published: Aug. 11, 2024

Trifluoromethyl heterocyclic compounds have high lipophilicity, metabolic stability and binding selectivity, so it is very important to develop their synthetic methods. This review provides an overview of synthesis trifluoromethyl substituted from β-trifluoromethylated acrylates over the period 2018 present.

Language: Английский

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