Radical-Mediated Tandem Cyclization to Construct Seven-Membered Nitrogen/Oxygen Heterocycles

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(12), P. 3995 - 3995

Published: Jan. 1, 2022

Owing to the special chemical structure of seven-membered heterocyclic skeleton and unique properties heteroatoms contained, it is widely used in natural products drug molecules.However, development synthetic methodology for these structures challenging due thermodynamic kinetic characteristics nitrogen/oxygen-containing frameworks, as well their own cross-ring forces.Therefore, great significance develop simple efficient methods construction compounds.Compared with traditional methods, radical reactions can avoid limitations poor atom economy harsh reaction conditions.In this review, recent strategies compounds using tandem cyclization are summarized.

Language: Английский

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Photoinduced Tandem Cyanomethylation/Cyclization of Unsaturated Compounds: Access to Cyanomethylated 7- or 5-Membered N-Heterocycles

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 12141 - 12149

Published: Aug. 2, 2023

A cyanomethylation/cyclization of aryl acetylenes/ethylenes with bromoacetonitrile was finished in a photopromoted condition, which offers an efficient and mild protocol for the preparation cyanomethylated 7- or 5-membered N-heterocycles good yields. Meanwhile, trichloroacetonitrile also compatible this radical pathway. In addition, variety single-crystal X-ray diffraction measurements, scaled-up operations to 1 mmol, functional group transformations final products, light on/off experiments, even radial inhibition studies were smoothly performed tandem system.

Language: Английский

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Et₂Zn-Mediated Radical (3 + 2) Cycloaddition of Vinyl Azides with Ethyl Iododifluoroacetate to Access 3,3-Difluoro-γ-lactams

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14634 - 14639

Published: Oct. 3, 2023

A diethylzinc-mediated radical (3 + 2) cycloaddition of vinyl azides with ethyl iododifluoroacetate is presented. The developed reaction features good functional group tolerance, broad substrate scope, and operational simplicity, enabling efficient assembly a wide range 3,3-difluoro-γ-lactam derivatives bearing an O-substituted quaternary carbon center in moderate to yields. utility the method showcased by scaled-up reaction, conversion product, late-stage structural modifications variety pharmaceutical compounds.

Language: Английский

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Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo trig cyclization, addition, elimination fashion.

Language: Английский

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Seven-membered rings

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 569 - 628

Published: Jan. 1, 2023

Language: Английский

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