Triple C–H Activation/Annulation: In Situ Construction of Fluorescent Peptides DOI

Zhefan Zhang,

Tianyan Wan,

Qi Quan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein, we report a Rh(III)-catalyzed triple C-H activation-annulation of Phe-based peptides with alkynes for the preparation fluorescent peptides. The robustness this protocol is reflected by broad substrate scope, high atom- and step-economy, excellent chemo- site-selectivity. An in situ generated polycyclic aromatic hydrocarbon carbocation as fluorophore exhibits good fluorescence properties (maximum emission wavelength up to 628 nm) low cell cytotoxicity. synthetic utility method further demonstrated versatile product applications bioconjugation protein BSA specifically targeting lysosomes mitochondria live mammalian cells.

Language: Английский

Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one DOI

Chun Xia Yang,

Bin Li, Peng Shi

et al.

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

Published: March 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Language: Английский

Citations

3
Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions DOI
Han Wang, Xiaolong Ma, Lingyi Sun

et al.

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096

Published: Jan. 9, 2025

Language: Английский

Citations

2
Advancements in hydroxyapatite synthesis and surface modifications for emerging biomedical applications DOI

Abdulkadhar Mohamed Jalaludeen,

Ramprasath Ramakrishnan,

Sivagaami Sundari Gunasekaran

et al.

Inorganic Chemistry Communications, Journal Year: 2024, Volume and Issue: 170, P. 113414 - 113414

Published: Nov. 4, 2024

Language: Английский

Citations

3
Unveiling the Synthesis of Indole-Fused Eight-Membered Aza-Heterocycles via FeCl3–Catalyzed Radical C–N Coupling and Photophysical Studies DOI
Sakshi Singh, Maitreya Maity, Shantanu Pal

et al.

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

Published: Feb. 25, 2025

A novel strategy toward construction of indole-fused eight-membered heterocyclic rings through a radical pathway has been reported. Our approach involves tandem cyclization via FeCl3-catalyzed cross-dehydrogenative double C–N bond formation using DDQ as an oxidant under mild condition. An EPR experiment and time course 1H NMR study confirm that the addition triggers pyrazole N-radical, which contributes to eight-member framework with good yield. The structural diversity synthetic utility have explored, along photophysical properties synthesized compounds.

Language: Английский

Citations

0
Catalytic System-Controlled [4 + 1] and [4 + 2] Annulation for the Construction of Pyrazolo[1,2-a]indazoles and Pyrazolo[1,2-a]cinnolines from Pyrazolidinones and Diazo Indandiones DOI
Qiang Xiao,

Shulei Hu,

Feifei Fang

et al.

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

Published: April 13, 2025

Pyrazolo[1,2-a]indazoles and pyrazolo[1,2-a]cinnolines can be constructed selectively via catalytic system-controlled C(sp2)-H activation/[4 + 1] cyclization 2] reaction, utilizing pyrazolidinones diazo indandiones. Employing two different Rh(III) catalysts, we successfully synthesized distinct types of nitrogen-containing heterocyclic compounds, pyrazolo[1,2-a]indazoles pyrazolo[1,2-a]cinnolines, respectively. Moreover, an inexpensive Ru(II) catalyst could also effectively generate with moderate to good yields. Overall, these methodologies offer advantages such as regioselectivity, broad substrate scope, operational simplicity, product availability.

Language: Английский

Citations

0
Synthesis of 3‐Hydroxyfluorenones Based on the Cascade Reaction of Aryl Enaminones with Benzyl Substituted Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu,

Shasha Ye

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: June 4, 2025

Comprehensive Summary Presented herein is a novel synthesis of 3‐hydroxyfluorenones through the cascade reaction aryl enaminones with benzyl substituted cyclopropanols. The formation product initiated by introduction an enone moiety onto enaminone cyclopropanol as homoenolate precursor C−H bond activation, followed intramolecular enamine Michael addition, enol amine elimination and aromatization‐driven oxidative dehydrogenation. To our knowledge, this should be first example for specific 3‐hydroxyfluorenone derivatives via simultaneous both indenone phenol scaffolds C−H/C−C/C−N activation three C−C formation. In general, newly developed protocol features easily accessible substrates, synthetically pharmaceutically valuable products, unique pathway, good compatibility various functional groups ready scalability.

Language: Английский

Citations

0
Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds DOI
Xiaogang Wang, Chi Yang, Di Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

A novel iridium-catalyzed [3 + 2] annulation of naphthylamines and α-diazocarbonyl compounds was developed for the rapid assembly densely functionalized indoles. This new catalytic process represents first example a cascade intramolecular nucleophilic cyclization by N-H insertion amines. Various could be obtained in high yields with excellent functional group tolerance. The reaction affords valuable indole derivatives, enabling expedient access to heterocyclic analogues not easily accessible other methods.

Language: Английский

Citations

1
Synthesis of [4.6] Spirocarbocycles: A Base-promoted Ring-Expansion and Subsequent I2-mediated Regioselective Spirocyclization Protocol DOI
Nana Fei, Zongkang Wang, Peng He

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6797 - 6803

Published: Jan. 1, 2024

An efficient protocol for the synthesis of [4.6] spirocarbocycles by reacting cyclic β-ketoesters with aryl-fused 1,6-diyn-3-ones has been developed.

Language: Английский

Citations

0
Triple C–H Activation/Annulation: In Situ Construction of Fluorescent Peptides DOI

Zhefan Zhang,

Tianyan Wan,

Qi Quan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein, we report a Rh(III)-catalyzed triple C-H activation-annulation of Phe-based peptides with alkynes for the preparation fluorescent peptides. The robustness this protocol is reflected by broad substrate scope, high atom- and step-economy, excellent chemo- site-selectivity. An in situ generated polycyclic aromatic hydrocarbon carbocation as fluorophore exhibits good fluorescence properties (maximum emission wavelength up to 628 nm) low cell cytotoxicity. synthetic utility method further demonstrated versatile product applications bioconjugation protein BSA specifically targeting lysosomes mitochondria live mammalian cells.

Language: Английский

Citations

0