A procedure has been developed for the regioselective, high yielding synthesis of 2H-indazoles that involves direct alkylation of indazoles with various allyl and benzyl bromides, and α-bromocarbonyl compounds.
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Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2-Indazoles.
J Org Chem
November 2024
Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Andrés M. del Río (IQAR), Facultad de Farmacia, Universidad de Alcalá, Alcalá de Henares, 28805 Madrid, Spain.
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C-N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step.
View Article and Find Full Text PDFDirect catalytic photodecarboxylative amination of carboxylic acids with diazirines for divergent access to nitrogen-containing compounds.
Cell Rep Phys Sci
August 2024
Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.
Amines, hydrazines, and nitrogen-containing heterocycles are pivotal species in medicine, agriculture, fine chemicals, and materials. Diazirines have been recently reported to serve as versatile electrophilic amination reagents for the synthesis of building blocks or late-stage C-N bond formation. Here, we report the catalytic photodecarboxylative amination of carboxylic acids with diazirines under mild conditions.
View Article and Find Full Text PDFGreen Approach for the Synthesis of 2-Phenyl-2-indazoles and Quinazoline Derivatives Using Sustainable Heterogeneous Copper Oxide Nanoparticles Supported on Activated Carbon and OER Study.
Langmuir
October 2024
Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Bangalore, Karnataka 562112, India.
This research work reports the synthesis of copper oxide (CuO) nanoparticles supported on activated carbon by a simple impregnation method using 2-propanol as a green solvent, followed by calcination. The synthesized CuO@C is used as an efficient heterogeneous nanocatalyst for the synthesis of 2-indazoles and quinazolines utilizing commercially available 2-bromobenzaldehydes, primary amines, and sodium azide under ligand-free and base-free conditions. The present methodology demonstrates the formation of new N-N, C-N, and C═N bonds under one-pot reaction conditions using PEG-400 as a green solvent.
View Article and Find Full Text PDFCatalyst-free photoarylation of 2-aryl-2-indazoles by carbon-iodine bond activation.
Org Biomol Chem
July 2024
Department of Fluoro & Agrochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500007, India.
Article Synopsis
- A new method has been developed to arylate 2-aryl-2-indazoles using aryl iodides without the need for a photocatalyst, yielding 3,2-diaryl-2-indazoles in good to moderate amounts.
- Potassium tert-butoxide plays a dual role in this reaction by activating the C-I bond and scavenging the HI byproduct generated during the process.
- This approach shows great versatility with accommodating various functional groups and has been successfully employed to create liver X receptor agonists and fluorescent probes, marking a significant advancement in the field.
Visible-Light-Driven Decarboxylative Coupling of 2-Indazoles with α-Keto Acids without Photocatalysts and Oxidants.
J Org Chem
May 2024
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China.
An efficient synthesis of functionalized 3-acyl-2-indazoles via visible-light-induced self-catalyzed energy transfer was developed. This method utilized a self-catalyzed energy transfer process between 2-indazoles and α-keto acids, offering advantages like absence of photosensitizers, metal catalysts, and strong oxidants, broad substrate compatibility, and operational simplicity under mild conditions.
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