Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

Visible-Light-Promoted α-C(sp3)–H Amidation of Cyclic Ethers under Redox-Neutral Conditions DOI
Shuangqing Li, Xiufang Xu, Jianhui Chen

et al.

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

Published: March 16, 2025

Reported herein is a visible-light-promoted strategy for the α-C(sp3)–H amidation of cyclic ethers using N-acyloxyamide as an oxidative amidating reagent. This transformation provides straightforward approach to various α-amidated under metal- and additive-free conditions. The synthetic utility products was demonstrated through facile transformations, including reduction, allylation, acylation, sulfonamidation, gram-scale reactions. Preliminary mechanistic studies suggest radical/radical cross-coupling process, with C(sp3)–H bond cleavage identified rate-determining step.

Language: Английский

Citations

1
Iodine-catalyzed intermolecular 1,2-thio (seleno)amination of alkenes with 1,2,3-triazoles and disulfides (diselenides) in air DOI
Jian Ji, Xuwen Chen,

Zongjing Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3066 - 3071

Published: Jan. 1, 2024

Iodine-catalyzed 1,2-thio (seleno)amination of alkenes via direct N- and C-centered radical cross-coupling was established to elicit highly regioselective β-triazolized thioalkyl compounds.

Language: Английский

Citations

5
Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles DOI
Yaqi Deng, Jian Xue, Xiang Wu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110822 - 110822

Published: Jan. 1, 2025

Language: Английский

Citations

0
N2-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control DOI
Hui Zhang, Zijian Zhang, Lifang Tian

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(6), P. 1428 - 1433

Published: Jan. 31, 2025

Herein, a relay strategy incorporating oxidative cross dehydrogenative coupling (CDC) and N1- to N2-isomerization is disclosed for the formal N2-selective alkylation of triazoles with ethers under thermodynamic control conditions. By taking advantage different thermodynamical stabilities N2-alkylated (3.65 kcal/mol), initially formed N1-isomers can be in situ converted into their more stable N2-isomers when reaching equilibrium. PhI(OAc)2 has been discovered function as both an oxidant CDC process efficient mediator isomerization step.

Language: Английский

Citations

0
Photoinduced Diazo Carbene-Promoted C(sp3)–H Oxidative Cross-Coupling Reaction for α-Triazolation of Isochromans DOI
Xiao Tang, Jinhua Liu, Xiang Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

A photocatalytic diazo triplet carbene-promoted C(sp3)–H oxidative coupling of isochromans and triazoles was developed in up to 83% yield at room temperature air. The radical-like carbenes were used as efficient HAT acceptors, the possible synergistic enabled unprecedented process with a high regioselectivity.

Language: Английский

Citations

0
Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates DOI Creative Commons
Changlei Zhu, Jiaxin Lin, Xiaoguang Bao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 4, 2025

In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type N-centered scavengers and apply them to the alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions features excellent functional group tolerance. It also enables preparation a range medicinally valuable amine derivatives from natural products. Further application this reagent in C-H amination, deoxygenative decarboxylative three component trifluoromethylative/sulfonylative aminations are realized. mechanistic studies DFT calculations conducted provide detailed evidence for mechanism.

Language: Английский

Citations

0
Design, synthesis, and in vitro evaluation of a carbamazepine derivative with antitumor potential in a model of Acute Lymphoblastic Leukemia DOI Creative Commons

Cristian Álvarez-Gómez,

Angela Fonseca-Benítez, James Guevara‐Pulido

et al.

PLoS ONE, Journal Year: 2025, Volume and Issue: 20(4), P. e0319415 - e0319415

Published: April 28, 2025

Acute lymphoblastic leukemia (ALL) is a significant concern in both pediatric and adult demographics. Despite 156 approved cancer therapies based on small molecules, mere five apply to all types of leukemia. Unfortunately, adherence these treatments low due adverse side effects. Consequently, there an urgent need identify more effective treatment options for ALL. This study presents potential solution. We have designed over fifty analogs carbamazepine, utilizing combination ligand-based structure-based drug design methodologies. Among analogs, we identified the CR80 analog, which demonstrated predicted binding values -8.66 kcal/mol against beta-tubulin, favorable LogP, IC 50 suitable vitro evaluation. The compound was synthesized with yield 50% subsequently assessed U-937 cell line. It obtained value 0.8 micromolar 1 selectivity index two, thus marking it as promising candidate vivo studies.

Language: Английский

Citations

0
Photoinduced Intermolecular Hydroamination and Hydroetherification of Electron‐Rich Alkenes With Low Catalyst Loadings DOI

You‐Qin Jiang,

Pei Qu,

Yong‐Hao Wang

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(22)

Published: July 24, 2024

Abstract A photochemical method based on visible‐light irradiation (blue LEDs/sunlight) has been developed for the intermolecular hydroamination and hydroetherification of electron‐rich alkenes. This is compatible with a wide range azoles alkenes, such as vinyl ethers, sulfides enamides, performed low concentrations photocatalyst (1000 ppm). Comprehensive mechanistic studies indicate that this process initiated by formation an active radical cation intermediate through single electron oxidation azole, which mediated excited Acr‐Mes + BF 4 − .

Language: Английский

Citations

2
Iodine(III)-Mediated Photochemical C–H Azolation DOI

Xuanzhen Han,

Wenjie Yue,

Zhixin Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9305 - 9310

Published: Oct. 23, 2024

A systematic radical polarity analysis framework is formulated herein for the projection of reactivity patterns. An iodine(III)-mediated photochemical C–H azolation reaction has been envisaged and developed based on set empirical guidelines. The synthesis features an environmentally benign reagent, mild conditions, operationally simple protocol, a broad substrate scope. inclusive demonstration ether, thioether, amide, benzylic, allylic bonds promises wide-ranging synthetic utility.

Language: Английский

Citations

2
Recent Developments on the Synthesis of Oxygen- and Sulfur-containing Heterocycles and their Derivatives under Visible Light Induced Reactions DOI
Tubai Ghosh, Sougata Santra, Grigory V. Zyryanov

et al.

Current Topics in Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 25(1), P. 124 - 140

Published: July 4, 2024

Visible-light-mediated reactions have recently emerged as a powerful strategy for the synthesis of diverse organic molecules under mild reaction conditions. Usually, are performed at room temperature and thus sensitive functional groups remain unaffected. Thus, this protocol has received intense interest from academia well industries. The heterocycles, in general, much because their biological activities application therapeutics. Oxygen- Sulfur-containing heterocyclic compounds attracted attention these showed promising anti-cancer drugs, antibiotics, antifungal anti-inflammatory agents among other applications. class by efficient greener routes become an important target. This review highlights various procedures derivatives visible light-induced reactions. green aspects mechanism each procedure been discussed.

Language: Английский

Citations

1