Direct Access to CF₃-Containing 4H-1,3-Oxazines and 2-Aminopyrimidines Via a [4 + 2] Annulation Using In Situ Generated Carbodiimide Anions

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The carbodiimide anions which were generated in situ from N-cyano-N-aryl-p-toluenesulfonamides (NCTS) the presence of base participated annulations that remain less reported to date. Herein, we have developed for first time an efficient and environmentally friendly [4 + 2] annulation reaction CF3-substituted hetero-1,3-dienes with NCTS synthesis 4H-1,3-oxazines 2-aminopyrimidines under transition-metal-free conditions. methodology demonstrates advantages readily available substrates, simple operation, good functional group tolerance, broad substrate scope, providing a promising route structurally diverse scaffolds. products followed by transformations provide facile TAS2R14 agonist analogues.

Language: Английский

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Easy Access to α,β-Diamino-Substituted Cyclopentenaminones through Copper-Catalyzed Double Amination of Unactivated Cyclic Ketones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 27, 2025

Here, we report a copper-catalyzed double amination of unactivated cyclic ketones with commercially available secondary arylamines for the synthesis α,β-diamino-substituted cyclopentenaminones. The direct intermolecular C-N bond formation reaction offers advantages using an inexpensive copper catalyst, high atom and step economy, mild conditions, convenient operation. Mechanistic experiments indicate that this α,β-difunctionalization proceeds through oxidative α-enamination/desaturation ketone one arylamine molecule to form α-enaminone intermediate, followed by another molecule.

Language: Английский

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Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16809 - 16827

Published: Nov. 1, 2024

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr4 for the synthesis bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation represents an efficient approach to construction 4-bromo-substituted with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, mild conditions. Mechanistic investigations show that this proceeds via cyclization enaminones followed by a regioselective bromination using as "Br" source.

Language: Английский

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Visible‐Light Enabled Synthesis of 1‐Aryl‐3‐Sulfonylmethyl‐1,2,4‐Triazoles by Arylazo Sulfones

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

Published: Nov. 5, 2024

Abstract We present a novel and highly efficient method for synthesizing polyfunctionalized 1,2,4‐triazoles. This approach leverages visible light arylazo sulfones in combination with N ‐vinyl amides, the environmentally friendly solvent ethyl acetate. Remarkably, reaction proceeds without need (photo)catalysts, ensuring near‐perfect atom economy producing only water as by‐product. exhibits excellent functional group tolerance can be scaled both batch continuous‐flow processes.

Language: Английский

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Nickel-Catalyzed Reductive Cyanation of Aryl Halides and Epoxides with Cyanogen Bromide

Molecules, Journal Year: 2024, Volume and Issue: 29(24), P. 6016 - 6016

Published: Dec. 20, 2024

Nitriles are valuable compounds because they have widespread applications in organic chemistry. This report details the nickel-catalyzed reductive cyanation of aryl halides and epoxides with cyanogen bromide for synthesis nitriles. robust protocol underscores practicality using a commercially available cost-effective reagent. A variety featuring diverse functional groups, such as -TMS, -Bpin, -OH, -NH2, -CN, -CHO, were successfully converted into nitriles moderate-to-good yields. Moreover, syntheses at gram-scale application late-stage natural products drugs reinforces its potentiality.

Language: Английский

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Overview of Phenylhydrazine‐Based Organic Transformations

ChemistrySelect, Journal Year: 2024, Volume and Issue: 10(1)

Published: Dec. 30, 2024

Abstract Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because the myriad applications, last decade has witnessed considerable upsurge interest perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some these have shown high regioselectivity in short reaction time under mild conditions. The emergence innumerable transformations utilizing phenylhydrazine unleashed numerous openings for development diverse heterocyclic scaffolds. Given importance this valuable chemical entity, review highlights methodologies Moreover, present article will considerably synthesis as well pharmaceutical chemistry. Academically, be interesting and informative researchers attempting develop new routes structures.

Language: Английский

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