Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3543 - 3548

Опубликована: Янв. 1, 2023

An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes with 2-bromoethan-1-ol as the brominating reagent has been developed.

Язык: Английский

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Electrochemically Mediated Carboxylative Cyclization of Allylic/Homoallylic Amines with CO₂ at Ambient Pressure

Organic Letters, Год журнала: 2022, Номер 24(44), С. 8239 - 8243

Опубликована: Ноя. 2, 2022

CO2 is an important C1 resource. We report a method for the synthesis of pharmacologically active 2-oxazolidinones by reacting with allylic amines. As opposed to previous addition reactions, unsaturated double bonds are preserved. Thus, product more plastic and easier use subsequent structural modification. Furthermore, this can also be applied six-membered heterocycles (1,3-oxazinan-2-ones) participation low concentration CO2, indicating it has certain practicability.

Язык: Английский

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Research progress in electrochemical/photochemical utilization of methanol as a C1 source

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8313 - 8327

Опубликована: Янв. 1, 2023

This review highlights the recent advances in various electrochemical and photochemical reactions using methanol as a sustainable C1 source.

Язык: Английский

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Electrochemical Dearomative Spirocyclization

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(9)

Опубликована: Март 15, 2023

Electrochemical dearomative spirocyclization serves as a green and sustainable approach to convert the flat, two-dimension aromatic feedstock into value-added three-dimension spirocyclic architectures. This review highlights recent advances, emphasizes mechanistic discussions, showcases synthetic applications of this emerging versatile powerful transformation.

Язык: Английский

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Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions

Bioorganic & Medicinal Chemistry Letters, Год журнала: 2025, Номер 119, С. 130096 - 130096

Опубликована: Янв. 9, 2025

Язык: Английский

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Research Advances in Electrochemical Synthesis of Spirocyclic Skeleton Compounds

Synthesis, Год журнала: 2023, Номер 55(18), С. 2873 - 2895

Опубликована: Янв. 24, 2023

Abstract Spirocyclic compounds have attracted the interest of synthetic chemists because their unique ring systems and utility in drug discovery. Many natural containing spirocyclic moieties skeleton are effective pharmaceuticals. For many redox processes, electroorganic synthesis is considered an environmentally friendly method, since use reagents with significant toxicity replaced by electric current, so amount waste often greatly reduced. Therefore, this review summarizes construction a via electrochemical strategies 2000. 1 Introduction 2 Electrochemically Mediated Synthesis Spirocyclopropanes 3 Spirooxindoles 4 Spirodienones 5 Other Heterospirocycles 6 Conclusion

Язык: Английский

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Total Synthesis of Aleutianamine

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(47), С. 25533 - 25537

Опубликована: Ноя. 15, 2023

Aleutianamine is a recently isolated pyrroloiminoquinone natural product that displays potent and selective biological activity toward human pancreatic cancer cells with an IC50 of 25 nM against PANC-1, making it potential candidate for therapeutic development. We report synthetic approach to aleutianamine wherein the unique [3.3.1] ring system tertiary sulfide this alkaloid were constructed via novel palladium-catalyzed dearomative thiophene functionalization. Other highlights synthesis include decarboxylative pinacol-type rearrangement allylic carbonate install ketone late-stage oxidative amination. This concise convergent strategy will enable access analogues further investigation product.

Язык: Английский

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Electrochemical N‐Aroylation of Sulfoximines by Using Benzoyl Hydrazines with H₂ Generation

Chemistry - A European Journal, Год журнала: 2023, Номер 30(9)

Опубликована: Ноя. 22, 2023

Abstract Developed here is a robust electrochemical cross‐coupling reaction between aroyl hydrazine and NH ‐sulfoximine via concomitant cleavage formation of C(sp 2 )−N bonds with the evolution H N as innocuous by‐products. This sustainable protocol avoids use toxic reagents occurs at room temperature. The proceeds generation an sulfoximidoyl radical anodic oxidation under constant current electrolysis (CCE), affording ‐aroylated sulfoximine. strategy applied to late‐stage sulfoximidation L‐menthol, (−)‐borneol, D‐glucose, vitamin‐E derivatives, marketed drugs such probenecid, ibuprofen, flurbiprofen, ciprofibrate, sulindac. In addition, present methodology mild, high functional group tolerance broad substrate scope scalable.

Язык: Английский

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Electrochemical Dearomative Amination of Phenol Derivatives: Access to Spirooxazolidinones

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(8), С. 1211 - 1216

Опубликована: Март 23, 2023

Abstract An electrochemical oxidative approach to spirooxazolidinones from phenol derivatives via intramolecular dearomative amination reactions is developed. This reaction proceeds without metal catalysts and external chemical oxidants, shows broad substrate scope diverse functional group compatibility. The synthetic utility of this strategy further exhibited by the gram‐scale synthesis late‐stage functionalization. By slightly tunning conditions, alcohols (1°, 2° 3°) can be afforded derivatives, which a good for deprotection para ‐methoxyphenyl (PMP) recover alcohol function. magnified image

Язык: Английский

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Radical Cyclization-initiated Difunctionalization Reactions of Alkenes and Alkynes

Опубликована: Апрель 15, 2024

Radical reactions are powerful in the synthesis of diverse molecular scaffolds bearing functional groups. In pervious review articles, we have presented 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6- and 1,7-difunctionalizations, addition followed by cyclization reactions. Presents this paper radical second functionalization The could be realized atom transfer reactions, or transition metal-assisted coupling with neutral molecules, cationic anionic species.

Язык: Английский

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