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

Catalytic Enantioselective Synthesis of Boron‐Stereogenic and Axially Chiral BODIPYs via Rhodium(II)‐Catalyzed C‐H (Hetero)Arylation with Diazonaphthoquinones and Diazoindenines DOI
Yankun Gao, Zizhen Liu, Sichao Tian

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

The molecular engineering of boron dipyrromethenes (BODIPYs) has garnered widespread attention due to their structural diversity enabling tailored physicochemical properties for optimal applications. However, catalytic enantioselective synthesis structurally diverse boron-stereogenic BODIPYs through intermolecular desymmetrization and with atroposelectivity remains elusive. Here, we showcase rhodium(II)-catalyzed site-specific C-H (hetero)arylations prochiral polysubstituted diazonaphthoquinonesand diazoindenines, providing efficient pathways the rapid assembly versatile (hetero)arylated axially chiral long-range axial rotational restriction modes. synthetic application procedures been emphasized by BODIPY derivatives various functions. Photophysical properties, bioimaging, lipid droplet-specific targeting capability are also demonstrated, indicating promising applications in biomedical research, medicinal chemistry, material science.

Language: Английский

Citations

4
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

0
Condition‐Controlled Selective Synthesis of CF3‐Chromene and CF3‐Benzofuran from N‐Phenoxyacetamide and CF3‐Ynone DOI Open Access

Huihang Hou,

Shengnan Yan,

Yuanshuang Xu

et al.

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

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

Citations

0
Furo[3,2-b]pyridine: Chemical synthesis, transformations and biological applications DOI Creative Commons

Sumayya Akram,

Sana Aslam, Nasır Rasool

et al.

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(5), P. 101906 - 101906

Published: July 20, 2024

The combination of heterocycles renders a new possibility to synthesize multicyclic compounds having improved biological activities. Furo[3,2-b]pyridine is fused heterocyclic ring system comprising furan attached at the third and second positions pyridine. These can be easily synthesized from versatile starting materials including pyridine, furan, benzofuran, benzopyridine via cycloaddition, cycloisomerization, multicomponent, cross-coupling, Dakin-type reactions by utilizing microwave, copper, palladium based catalysts. Among chemical transformations furo[3,2-b]pyridine derivatives, review covered acetylation, addition, condensation, chlorination, Suzuki coupling, Vilsmeier-Haack reaction, nucleophilic substitution reactions. has attracted remarkable attention researchers due its wide range pharmacological applications as antibiotic, antiviral, antifungal, anticancer, inhibitors nicotinic acetylcholine receptors, CLKs, e1F4A, DYRKIA, α-glucosidase β-glucosidase. purpose discuss chemistry title reported during 2019–2024.

Language: Английский

Citations

1
Microwave-Assisted Palladium-Catalyzed Crossover-Annulation: Access to Fused Polycyclic Benzofuran Scaffolds DOI

Komal Goel,

Gedu Satyanarayana

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

Published: Dec. 25, 2024

This study demonstrates quick access to heteroatom-embodied complex fused polycyclic frameworks through a palladium-catalyzed domino process facilitated by microwave-assisted crossover annulation of o-alkynylarylhalides and dihydrobenzofurans derivatives. The overall success this lies in the careful design dihydrobenzofuran precursors that direct initial palladium-mediated step proceed highly regioselective manner furnish single regioisomeric product. Notably, one-pot method has witnessed good substrate scope furnished products with excellent yields.

Language: Английский

Citations

1
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
Catalytic Enantioselective Synthesis of Boron‐Stereogenic and Axially Chiral BODIPYs via Rhodium(II)‐Catalyzed C‐H (Hetero)Arylation with Diazonaphthoquinones and Diazoindenines DOI
Yankun Gao, Zizhen Liu, Sichao Tian

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract The molecular engineering of boron dipyrromethenes (BODIPYs) has garnered widespread attention due to their structural diversity enabling tailored physicochemical properties for optimal applications. However, catalytic enantioselective synthesis structurally diverse boron‐stereogenic BODIPYs through intermolecular desymmetrization and with atroposelectivity remains elusive. Here, we showcase rhodium(II)‐catalyzed site‐specific C−H (hetero)arylations prochiral polysubstituted diazonaphthoquinonesand diazoindenines, providing efficient pathways the rapid assembly versatile (hetero)arylated axially chiral long‐range axial rotational restriction modes. synthetic application procedures been emphasized by BODIPY derivatives various functions. Photophysical properties, bioimaging, lipid droplet‐specific targeting capability are also demonstrated, indicating promising applications in biomedical research, medicinal chemistry, material science.

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

0