The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16613 - 16621
Published: Oct. 31, 2024
A practical approach for rapid and efficient access to spirocyclic isobenzofurans is described. The reaction proceeds through the cycloaddition of 1,6-ynenone derivatives 4-nitro-1,3-diarylbutan-1-ones, promoted by Cs
Language: Английский
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3543 - 3548
Published: Jan. 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.
Language: Английский
Citations
50
Organic Letters, Journal Year: 2022, Volume and Issue: 24(44), P. 8239 - 8243
Published: Nov. 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.
Language: Английский
Citations
49
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8313 - 8327
Published: Jan. 1, 2023
This review highlights the recent advances in various electrochemical and photochemical reactions using methanol as a sustainable C1 source.
Language: Английский
Citations
39
Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(9)
Published: March 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.
Language: Английский
Citations
36
Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096
Published: Jan. 9, 2025
Language: Английский
Citations
1
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(47), P. 25533 - 25537
Published: Nov. 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.
Language: Английский
Citations
11
Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2873 - 2895
Published: Jan. 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
Language: Английский
Citations
10
Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(9)
Published: Nov. 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.
Language: Английский
Citations
7
Published: April 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.
Language: Английский
Citations
2
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(8), P. 1211 - 1216
Published: March 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
Language: Английский
Citations
5