Molecular-iodine catalyzed selective construction of cyclopenta[b]indoles from indoles and acetone: a green gateway to indole-fused cycles DOI

Prantika Bhattacharjee,

Bipul Sarma, Utpal Bora

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9275 - 9285

Published: Jan. 1, 2023

Molecular-iodine catalyzed access to an important class of bio-relevant indole derivatives, cyclopenta[b]indoles, has been achieved via a cascade addition/intramolecular cyclization reaction indoles and acetone. Explorations diverse substitution patterns revealed essential substrate-control in the reaction. The high-density electronic core is pivotal favouring formation indolyl-cyclopenta[b]indole derivatives; contrast, electron deficiency hindered process, directing bis(indolyl)propanes. Investigations on mechanistic pathway that bis(indolyl)alkanes were intermediates for addition-cyclization process. This simple experimental method provides sustainable synthetic cyclopentannulated indoles.

Language: Английский

Review of application of the I2 and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations DOI
Dongsheng Yang, Xiang‐Long Chen, An‐Xin Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2665 - 2692

Published: Jan. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Language: Английский

Citations

16
I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis DOI Creative Commons

Rakshanda Singhal,

Satya Prakash Choudhary,

Babita Malik

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(9), P. 5817 - 5845

Published: Jan. 1, 2024

A variety of bioactive compounds can be synthesized via C–C and C–X (X = O/S/N/Se/Cl/Br) bond formation using an efficient catalytic system I 2 /DMSO. This review highlights the progress identifies potential paths for future research in this field.

Language: Английский

Citations

12
An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents DOI Creative Commons
Mohammad Saquib, Shakir Ahamad, Mohammad Faheem Khan

et al.

Frontiers in Pharmacology, Journal Year: 2023, Volume and Issue: 14

Published: May 5, 2023

Herein, we report an efficient and eco-friendly, ultrasound assisted synthetic strategy for the construction of diversified pyrrolobenzodiazepine-triazole hybrids, which are potentially pharmaceutically important scaffolds, via a domino reaction involving intermolecular electrophilic substitution followed by intramolecular Huisgen 1,3-dipolar azide-alkyne cycloaddition. The USP reported protocol is use benign inexpensive, recyclable molecular iodine-ionic liquid synergistic catalytic system cum media achieving synthesis. other salient features this method mild conditions, high yield atom economy, operational simplicity, broad substrate scope easy workup purification. All synthesized compounds were evaluated in vitro anti-proliferative activity against various cancer cell lines. From among title compounds, 9,9-dimethyl-8-phenyl-9H-benzo [b]pyrrolo [1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine (7) was found most to be active compound exhibiting IC50 value 6.60, 5.45, 7.85, 11.21, 12.24, 10.12, 11.32 µM MCF-7, MDA-MB-231, HeLa, SKOV-3, A549, HCT-116 DLD-1 lines, respectively. Further non-toxic normal human embryonic kidney (HEK-293) line.

Language: Английский

Citations

21
Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation DOI
Swadhin Swaraj Acharya,

Sagarika Patra,

Liza Mama Barad

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(17), P. 7614 - 7638

Published: Jan. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Language: Английский

Citations

7
Multicomponent hydrosulfonylation of alkynes for the synthesis of vinyl sulfones DOI
Mei Lan,

Xiao-Rong Shu,

Fa-Liang Liu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8820 - 8825

Published: Jan. 1, 2023

An efficient and mild multicomponent reaction (MCR) for the preparation of vinyl sulfones achieved by carrying out hydrosulfonylation alkynes with corresponding aryl diazonium salts, K 2 S O 5 thiophenols at room temperature without any metal catalysts or additives.

Language: Английский

Citations

13
Facile synthesis of the unknown 6,7-dihydrofuro[3,4-c]pyridines and 3,4-diaryloylpyridines from N-propargyl β-enaminones DOI Creative Commons
Elif Serel Yilmaz, Kerem Kaya, Metin Zora

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A simple methodology for the synthesis of bicyclic 6,7-dihydrofuro[3,4- c ]pyridines is reported. The skeletal diversity synthesized heterobicyclic frame may present new nitrogen- and oxygen-based hybrid systems medicinal chemistry.

Language: Английский

Citations

0
Molecular Iodine-Catalyzed Synthesis of 3,3-Disubstituted Isatins: Total Synthesis of Indole Alkaloid, 3,3-Dimethoxy-2-oxindole DOI Creative Commons
Keisuke Tokushige, Shota Asai, Takumi Abe

et al.

Chemistry, Journal Year: 2025, Volume and Issue: 7(2), P. 43 - 43

Published: March 17, 2025

3,3-Dialkoxy-2-oxindoles are prevalent in natural products and exhibit unique biological activities. Among them, acyclic alkoxy analogues show instability acidic conditions, making access to isatin ketals highly challenging. Conventional methods for the synthesis of 3,3-dialkoxy-2-oxindoles usually require strongly harsh reaction resulting a low overall efficiency. Herein, we report on an acid- metal-free protocol from isatins through iodine-catalyzed ketalization. This photochemical does not use any specific reagents such as metal catalysts. Furthermore, total unprecedented 2-oxindole alkaloid bearing 3,3-dimethoxy moiety is achieved.

Language: Английский

Citations

0
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
Metalated covalent organic frameworks as efficient catalysts for multicomponent tandem reactions DOI

Xuan Kan,

Jian‐Cheng Wang, Yu‐Bin Dong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(50), P. 6362 - 6374

Published: Jan. 1, 2024

Multicomponent tandem reactions have become indispensable synthetic methods due to their economic advantages and efficient usage in natural products drug synthesis. The emergence of metalated covalent organic frameworks (MCOFs) has opened up new opportunities for the advancement multicomponent reactions. In contrast commonly used homogeneous transition metal catalysts, MCOFs possess regular porosity, high crystallinity, rich chelation sites that facilitate uniform distribution anchoring metals within cavities. Thus, they show extremely activity recently been widely employed as catalysts It is timely conduct a review reactions, order offer guidance assistance synthesis MCOF application This provides comprehensive overview design MCOFs, progress primary challenges encountered during current development with aim contributing promotion field.

Language: Английский

Citations

3
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