Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5538 - 5544
Published: Jan. 1, 2024
A defluorinative 1,2,3,4-tetrafunctionalization of perfluoroalkyl alkenes with readily available ureas via multi-bond interconversion at four carbon sites has been developed for the synthesis perfluoroalkenyl 2-imidazolones.
Language: Английский
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 26, 2025
A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.
Language: Английский
Citations
1
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5144 - 5150
Published: Jan. 1, 2024
A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.
Language: Английский
Citations
4
Biology of Sex Differences, Journal Year: 2025, Volume and Issue: 16(1)
Published: Feb. 21, 2025
Abstract Background Accumulating evidence indicates that the dysbiosis of gastrointestinal microbiota is associated with development gastric carcinogenesis. However, sex-specific traits and their correlation sexually dimorphic response to cancer remain poorly understood. Methods Male female transgenic FVB/N insulin-gastrin (INS-GAS) mice as a model were randomly administered Brucella Broth or Helicobacter pylori ( H. ). Stomachs evaluated by histopathology. The inflammation was examined immunohistochemical immunofluorescence staining. Gastric mucosal fecal samples collected for analysis using 16S rRNA gene sequencing. Results Following infection, male showed heightened inflammatory infiltration notably greater intestinal metaplasia compared mice. structure different between mice, relative higher diversity in females than males. Notably, we found gender disparities alterations post infection. While enrichment Bifidobacterium Lachnospiraceae observed Escherichia_Shigella Akkermansia more abundant Furthermore, microbial profile distinct estrogen-deficient ovariectomized (OVX) including overgrowth loss Butyricicoccus . Infected OVX developed significantly severe lesions, which normalized through co-housing intact females. Conclusions We have identified novel microbiome-based mechanism provides insight into sexual dimorphism -associated cancer.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 23, 2025
Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones biocompatible sodium sulfinates has been developed for the modular synthesis densely functionalized furans with regio-defined C2,4-bissulfonyl C3-trifluoromethyl substitutions. This three-component method proceeds through sequential sulfonylation intramolecular O-cyclization, enabling assembly one furan ring, formation C-SO2/C–O bonds, cleavage three C(sp3)-F bonds one-pot manner under transition metal-free conditions. Moreover, obtained product can further react benzyne precursor to generate 1,4-epoxynaphthalene Diels–Alder cycloaddition. The is also distinguished by its broad substrate scope, excellent functional group tolerance, scalability.
Language: Английский
Citations
0
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
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 24, 2025
The δ-lactam motif is a privileged pharmacophore in drug design and development. While these biologically relevant molecules could be assembled through two-component cyclization, modular approach to constructing structures via multicomponent reaction with unactivated alkenes as starting materials rare. Herein, we report tandem that integrates alkene-dialkylation radical-involved ring-opening cyclization under single metal-electron-shuttle catalysis, which represents the most expeditious access fluorinated δ-lactams from simple alkenes.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 28, 2025
Pyridines represent privileged heterocycles, and the ability to produce fluorinated pyridines from polyfluorinated substances through selective defluorofunctionalization is a new addition their synthesis. Herein, an unprecedented formal [4+2] defluorocycloaddition of perfluoroalkyl alkynes benzylamines under metal-free conditions described. By leveraging functionalization four C(sp3)–F bonds on two vicinal sterically hindered carbons alkynes, diverse array meta-fluoroalkylated pyridin-4-amines were synthesized with good functional group tolerance. The mechanistic studies revealed sequence hydroamination, successive defluorination, 6π-electrocyclization, aromatization, amination.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 9, 2025
Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation PFAIs with sulfonamides for chemo-, regio-, Z-stereoselective synthesis valuable β-fluoroacyl vinylamines. This reaction proceeded via sequential deiodoamination defluoroxylation process under transition-metal-free conditions, featuring broad substrate scope good functional group tolerance. Compared to reported methods, some drawbacks, such multistep manipulation, harsh need expensive catalysts, use toxic/sensitive could be eliminated. Furthermore, synthetic potential this method was demonstrated scale-up synthesis, postfunctionalization complex molecules, ready transformation products.
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5538 - 5544
Published: Jan. 1, 2024
A defluorinative 1,2,3,4-tetrafunctionalization of perfluoroalkyl alkenes with readily available ureas via multi-bond interconversion at four carbon sites has been developed for the synthesis perfluoroalkenyl 2-imidazolones.
Language: Английский
Citations
3