Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2<i>H</i>‐Indazoles from 2‐Alkynylazobenzenes DOI Creative Commons
Clara Mañas, Estı́baliz Merino

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract We disclose the intramolecular synthesis of 3‐alkenyl‐2 H ‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl 3 and ruthenium photocatalyst under visible light irradiation. This reaction proceeds through hydroamination alkynyl fragment. The yields are influenced electronic factors. Control experiments suggest that both radical polar mechanisms operate in parallel. transformation involves C−N bond formation 1,2‐hydride shift. Additionally, derivatization was performed to demonstrate versatility this methodology.

Language: Английский

Visible‐light‐mediated synthesis of 2H-indazoles from (2-Bromo-benzylidene)-phenyl-amine derivatives by the Ullmann Goldberg reaction. DOI
Ali Akbari,

Danial Zand Hosein shahi,

Ali Rahimabadi

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134486 - 134486

Published: Jan. 1, 2025

Language: Английский

Citations

0
Direct Deoxygenative C-N Coupling to Construct Indazole under Visible Light DOI

Xinluo Song,

Lingfeng Yin,

Subin Hao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The green synthesis of medicines with an indazole skeleton has gained significant attention in recent years.

Language: Английский

Citations

2
Synergistic Synthesis and Computational Analysis of Novel Indazole-2-Pyrone Hybrids: Toxicity, Hirshfeld Surface Insights, and Antiviral Potential against HIV-1 and Coronaviruses DOI
Mohamed El Ghozlani, Yassine Hakmaoui, Abdellatif Rafik

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1321, P. 139900 - 139900

Published: Sept. 8, 2024

Language: Английский

Citations

2
Shaping cycles with light: a regiodivergent approach to tetracyclic aza-aromatic compounds DOI Creative Commons
Clara Mañas,

Belén Ibarra,

Estı́baliz Merino

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

We present a novel visible light-promoted regiodivergent cyclization, enabling the selective synthesis of distinct azapolyaromatic regioisomers from 2-alkynlazobenzenes.

Language: Английский

Citations

1
Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2H-Indazoles DOI Creative Commons
Clara Mañas,

Juan Herrero-Bourdieu,

Estı́baliz Merino

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16883 - 16888

Published: Nov. 2, 2024

A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C–N bond formation and subsequent 1,2-hydride shift, affording products high yields. DFT calculations suggest the shift as rate-determining step. Further derivatization enables functionalization 3-alkenyl-2H-indazoles.

Language: Английский

Citations

1
Photo- and Electro-chemical Strategies for Indazole Synthesis DOI Creative Commons
Binbin Huang

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: unknown, P. 100116 - 100116

Published: Dec. 1, 2024

The indazole core is prevalently found in the structures of bioactive molecules, demonstrating promising potential medicinal chemistry and drug discovery, which therefore has attracted sustained attention from synthetic community. Over recent decades, significant progress been achieved both organic photocatalysis electrosynthesis, offering novel approaches for efficient sustainable synthesis various functionalized indazoles. This mini-review highlights emerging methodological advancements photo-/electro-chemical two common forms indazole, namely 1H- 2H-indazoles, are classified by specific intramolecular bond formation patterns: (1) C-C formation, (2) C-N (3) N-N formation. reaction conditions, representative scopes, mechanistic understandings these protocols emphasized, to elucidate advantages limitations current strategies, with an aim inspire future innovations that may address challenges modern synthesis.Graphical abstractTo create your abstract, type over instructions template box below. Fonts or abstract dimensions should not be changed altered.

Language: Английский

Citations

1
Visible‐Light‐Mediated Synthesis of 2h-Indazoles from (2-Bromo-Benzylidene)-Phenyl-Amine Derivatives by the Ullmann Goldberg Reaction DOI
Ali Akbari,

Danial Zand Hosein shahi,

Ali Rahimabadi

et al.

Published: Jan. 1, 2024

Language: Английский

Citations

0
Combined Gold and Photoredox Catalysis: Synthesis of 3‐Alkenyl‐2<i>H</i>‐Indazoles from 2‐Alkynylazobenzenes DOI Creative Commons
Clara Mañas, Estı́baliz Merino

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract We disclose the intramolecular synthesis of 3‐alkenyl‐2 H ‐indazoles from 2‐alkynylazobenzenes, promoted by a dual catalysis using AuCl 3 and ruthenium photocatalyst under visible light irradiation. This reaction proceeds through hydroamination alkynyl fragment. The yields are influenced electronic factors. Control experiments suggest that both radical polar mechanisms operate in parallel. transformation involves C−N bond formation 1,2‐hydride shift. Additionally, derivatization was performed to demonstrate versatility this methodology.

Language: Английский

Citations

0