Construction of Benzoxazole and Isoquinoline Compounds via Base-Mediated Cyclization of Amino Acid Derivatives

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

Published: March 19, 2025

Biological organisms contain bioactive macromolecules such as amino acids, which serve basic materials for constructing cells and repairing tissues. Due to the unique properties of fluorine atom, can alter structure proteins increase their lipophilicity, incorporating a atom into acids has become research hotspot. In this study, ethyl 3-bromo-2-((diphenylmethylene)amino)-3,3-difluoropropanoate was synthesized from glycine derivatives. Under alkaline conditions, compound reacted with 2-aminophenol generate benzoxazole-containing acid derivative. This method is simple operate, without metal participation, performed under relatively eco-friendly reaction providing novel approach synthesis benzoxazole heterocycles.

Language: Английский

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A highly efficient approach to Z-monofluoroolefin-dehydroamino acid derivatives from gem-difluoroalkenes

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111167 - 111167

Published: April 1, 2025

Language: Английский

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Stereoselective Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Tetrasubstituted gem-Difluoroalkenes

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 376 - 379

Published: Dec. 28, 2023

We herein describe a diastereoselective Pd(0)-catalyzed Hiyama cross-coupling reaction of gem-difluoroalkenes. The use organosilicon reagents in this is advantageous over other organometallic by allowing the introduction wide range functional groups, including challenging alkyl groups. Also conveniently, additive TBAF was not required for (hetero)aryl-substituted difluoroalkenes.

Language: Английский

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Addition of Carboxylic Acids to gem-Difluoroalkenes for the Synthesis of gem-Difluoromethylenated Compounds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1261 - 1264

Published: Feb. 1, 2024

We herein describe a straightforward protocol for the synthesis of carboxylic esters containing gem-difluoromethylene unit. Readily available acids can act as nucleophiles to add regioselectively tetrasubstituted or trisubstituted β,β-difluoroacrylates (formal hydroacetoxylation) construction RCO2–CF2 bonds. Thermal conditions are sufficient without use catalysts additives.

Language: Английский

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Palladium-Catalyzed Defluorinative Alkylation of gem-Difluoroalkenes with Cyclopropanols: Stereoselective Synthesis of γ-Fluorinated γ,δ-Unsaturated Ketones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3591 - 3596

Published: April 25, 2024

A palladium-catalyzed defluorinative alkylation of gem-difluoroalkenes with cyclopropyl alcohols was developed. range γ-fluorinated γ,δ-unsaturated ketones were constructed in good yields excellent stereoselectivities. In addition, by base-mediated intramolecular nucleophilic vinylic substitution (SNV), the products could be further transformed to 2,5-dimethylenetetrahydrofurans and analogues

Language: Английский

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Stereodivergent Palladium-Catalyzed C–F Bond Functionalization of gem-Difluoroalkenes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5822 - 5826

Published: June 27, 2024

We herein describe a stereodivergent C-F bond functionalization of

Language: Английский

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Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2691 - 2703

Published: Oct. 24, 2024

In this study, we develop the synthesis methods of fluoroalkenes and fluoroenynes via Suzuki–Miyaura Sonogashira cross-coupling reactions using novel multihalogenated fluorovinyl ethers, which are easily prepared from reaction between phenols 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane). These make use unique structure contains a reactive bromine atom, to afford series in moderate high yields.

Language: Английский

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Access to Fluorinated Dienes through Hydrofluorination of 2-En-4-ynoates

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

The hydrofluorination of enynoates has been developed for the synthesis fluorinated dienoates.

Language: Английский

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