Iron-Catalyzed Thioarylation of Arenes Using Saccharin-Derived Reagents DOI Creative Commons
Lachlan J. N. Waddell, Oluwajuwon A. M. Okunade,

Amy C. Dodds

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 16, 2025

Biaryl sulfides are important scaffolds found in various natural products and pharmaceutically active compounds. One of the main approaches for synthesis this compound class involves substitution arenes using electrophilic thioaryl species. However, these methods generally require acidic activation electrophile, more forcing conditions, long reaction times. Here, we describe combination super Lewis acid iron(III) triflimide with saccharin-based thioarylation reagents rapid unsymmetrical biaryl under mild conditions. This approach was effective electron-deficient species that performed poorly previous methods, allowing efficient functionalization bioactive

Язык: Английский

I2-Catalyzed Cascade Annulation/Cross-Dehydrogenative Coupling: Excellent Platform to Access 3-Sulfenyl Pyrazolo[1,5-a]pyrimidines with Potent Antibacterial Activity against Pseudomonas aeruginosa and Staphylococcus aureus DOI

Suvam Paul,

Samik Biswas,

Tathagata Choudhuri

и другие.

ACS Applied Bio Materials, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

The increasing resistance of bacteria to antibiotics has become a serious threat existing options for treating bacterial infections. We have developed synthetic methodology 3-sulfenyl pyrazolo[1,5-a]pyrimidines with potent antibacterial activity. This iodine-catalyzed strategy been by employing amino pyrazoles, enaminones/chalcones, and thiophenols through intermolecular cyclization subsequent cross-dehydrogenative sulfenylation. highly regioselective practicable protocol utilized synthesize structurally diverse wide functionalities. is also extendable toward the synthesis bis(pyrazolo[1,5-a]pyrimidin-3-yl)sulfanes from pyrazole, enaminones/chalcone, KSCN pyrazolo[1,5-a]pyrimidine direct acetophenone. Mechanistic investigation disclosed radical pathway C-H sulfenylation involvement 3-iodo as active intermediate. biological activity sulfenyl against Pseudomonas aeruginosa Staphylococcus aureus, whereas sulfinyl no such Sulfenyl mechanistically inhibited growth accumulation ROS well induction in lipid peroxidation. Subsequently, circumstances changed membrane potential facilitated interaction membrane-associated proteins, leading loss integrity damage cell membranes. Moreover, these derivatives potentiated efficacy commercial antibiotic ciprofloxacin selected strains can be considered an alternative therapy

Язык: Английский

Процитировано

0
Iron-Catalyzed Thioarylation of Arenes Using Saccharin-Derived Reagents DOI Creative Commons
Lachlan J. N. Waddell, Oluwajuwon A. M. Okunade,

Amy C. Dodds

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 16, 2025

Biaryl sulfides are important scaffolds found in various natural products and pharmaceutically active compounds. One of the main approaches for synthesis this compound class involves substitution arenes using electrophilic thioaryl species. However, these methods generally require acidic activation electrophile, more forcing conditions, long reaction times. Here, we describe combination super Lewis acid iron(III) triflimide with saccharin-based thioarylation reagents rapid unsymmetrical biaryl under mild conditions. This approach was effective electron-deficient species that performed poorly previous methods, allowing efficient functionalization bioactive

Язык: Английский

Процитировано

0