PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes DOI

Suvam Paul,

Sourav Das,

Tathagata Choudhuri

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 4, 2024

We have developed a visible-light-mediated convenient and efficient strategy for the iodination of heteroarenes using diacetoxyiodobenzene (PIDA) under photocatalyst-free conditions. This unique approach is first report on photocatalytic C-H employing PIDA as iodinating agent. The new applicable to wide range pyrazolo[1,5-a]pyrimidine derivatives with various functionalities. Iodination other electron-rich heterocycles like imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, pyrazoles has been accomplished this benign protocol. usefulness 3-iodo synthetic intermediate in synthesizing functionalized pyrazolo[1,5-a]pyrimidines demonstrated.

Language: Английский

Advances in pyrazolo[1,5-a]pyrimidines: synthesis and their role as protein kinase inhibitors in cancer treatment DOI Creative Commons

Terungwa H. Iorkula,

Osasere Jude-Kelly Osayawe,

Daniel A. Odogwu

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(5), P. 3756 - 3828

Published: Jan. 1, 2025

Pyrazolo[1,5- a ]pyrimidines are notable class of heterocyclic compounds with potent protein kinase inhibitor (PKI) activity, playing critical role in targeted cancer therapy.

Language: Английский

Citations

2
Aggregation-induced emission materials-based Electrochemiluminescence emitters for sensing applications: Progress, challenges and perspectives DOI
Xuan Wang,

Rongyan Wan,

Yan Tang

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 531, P. 216520 - 216520

Published: Feb. 12, 2025

Language: Английский

Citations

1
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

et al.

ACS Applied Bio Materials, Journal Year: 2025, Volume and Issue: unknown

Published: March 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

Language: Английский

Citations

0
Tunable Regioselective Allylic Alkylation/Iodination of Imidazoheterocycles in Water DOI

Suvam Paul,

Tathagata Choudhuri,

Sourav Das

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1492 - 1504

Published: Jan. 12, 2024

The switchable roles of allylic alcohol and molecular iodine as reagents catalysts have been demonstrated in the regioselective alkylation iodination imidazoheterocycles employing mixture alcohol-I2. First, we explored catalytic activity for allylation using an aqueous medium. a library other electron-rich heterocycles like indole, pyrazole, 4-hydroxy coumarin, 6-amino uracil has achieved by this methodology. efficiency I2 catalyst N-allylation azoles also demonstrated. Next, shown that could be beneficial under room temperature. Mechanistic studies indicate activation took place probably through halogen bonding, NMR show reaction did not proceed ether formation.

Language: Английский

Citations

1
Regioselective C(sp2)–H halogenation of pyrazolo[1,5-a]pyrimidines facilitated by hypervalent iodine(iii) under aqueous and ambient conditions DOI Creative Commons

Abhinay S. Chillal,

Rajesh T. Bhawale,

Umesh A. Kshirsagar

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(19), P. 13095 - 13099

Published: Jan. 1, 2024

An efficient and mild approach has been developed for the regio-selective direct C3 halogenation of pyrazolo[1,5- a ]pyrimidines employing readily available potassium halide salts hypervalent iodine( iii ) reagent at ambient temperature.

Language: Английский

Citations

1
I2-Catalyzed Three-Component Synthesis of 3-Selenylated Pyrazolo[1,5-a]pyrimidines DOI

Tathagata Choudhuri,

Suvam Paul,

Papiya Sikdar

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(21), P. 9480 - 9485

Published: Jan. 1, 2024

A one-pot strategy has been developed for the synthesis of 3-selenylated pyrazolo[1,5- a ]pyrimidines from amino pyrazoles, chalcones/enaminones, and diselenides through I 2 -catalyzed tandem cascade annulations/C–H selenylation.

Language: Английский

Citations

1
Visible‐Light‐Mediated Oxidative Desulfurization‐Oxygenation in Cyclic Thio‐Amide DOI
Partha Pratim Das, Paramita Das, Souvik Mondal

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(18)

Published: May 6, 2024

Abstract Visible‐light assisted a very simple and mild protocol for photocatalytic oxidative transformation of thioamide to amide group has been realized in cyclic system. For this purpose 5‐arylalkylidene‐rhodanine derivatives were chosen as model substrates afford thiazolidine‐2,4‐diones. Light mediated reactions are intrinsically beneficial, since activation occurs by cleanest energy source light. Here K 2 S O 8 is used terminal oxidant which does not leave any hazardous corrosive waste discard after the reaction fostering practices green chemistry. This first report conversion thioxo rhodanine into corresponding oxygen analogue visible light photo‐catalytic method. The was general various 5‐arylalkylidene‐rhodanines underwent smoothly affording high product yields. Moreover, broadness further established applying on other systems like 3,4‐dihydropyrimidine‐2(1H)‐(thio)ones.

Language: Английский

Citations

1
PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes DOI

Suvam Paul,

Sourav Das,

Tathagata Choudhuri

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 4, 2024

We have developed a visible-light-mediated convenient and efficient strategy for the iodination of heteroarenes using diacetoxyiodobenzene (PIDA) under photocatalyst-free conditions. This unique approach is first report on photocatalytic C-H employing PIDA as iodinating agent. The new applicable to wide range pyrazolo[1,5-a]pyrimidine derivatives with various functionalities. Iodination other electron-rich heterocycles like imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, pyrazoles has been accomplished this benign protocol. usefulness 3-iodo synthetic intermediate in synthesizing functionalized pyrazolo[1,5-a]pyrimidines demonstrated.

Language: Английский

Citations

1