Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in...

Full description

Bibliographic Details
Main Authors:	Geetanjali S. Sontakke, Rahul K. Shukla, Chandra M. R. Volla
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-02-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	amination heteroarylation quinoline n-oxides regioselective triazoles
Online Access:	https://doi.org/10.3762/bjoc.17.42

Similar Items

Synthesis and Biological Activity of 3-(Heteroaryl)quinolin-2(1<i>H</i>)-ones Bis-Heterocycles as Potential Inhibitors of the Protein Folding Machinery Hsp90
by: Enrique L. Larghi, et al.
Published: (2022-01-01)

Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation
by: Hoong-Kun Fun, et al.
Published: (2013-10-01)

Experimental and In Silico Evaluation of New Heteroaryl Benzothiazole Derivatives as Antimicrobial Agents
by: Alexander Zubenko, et al.
Published: (2022-11-01)

QUINOLIN-6-AMINES: SYNTHESIS AND BIOLOGICAL EVALUATION
by: Hament Panwar, et al.
Published: (2013-12-01)

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors
by: Lamya H. Al-Wahaibi, et al.
Published: (2021-04-01)

2-((Pyren-1-ylmethylamino)methyl)quinolin-8-ol
by: Carlos Lodeiro, et al.
Published: (2010-10-01)

Synthesis, Antioxidant and Antiproliferative Actions of 4-(1,2,3-Triazol-1-yl)quinolin-2(1<i>H</i>)-ones as Multi-Target Inhibitors
by: Essmat M. El-Sheref, et al.
Published: (2023-08-01)

Heteroaryl-Ethylenes as New Effective Agents for High Priority Gram-Positive and Gram-Negative Bacterial Clinical Isolates
by: Dalida Angela Bivona, et al.
Published: (2022-06-01)

Synthesis and Antimicrobial Activity of New Heteroaryl(aryl) Thiazole Derivatives Molecular Docking Studies
by: Victor Kartsev, et al.
Published: (2022-09-01)

A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids
by: Halyna Hryhoriv, et al.
Published: (2023-03-01)

New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies
by: Yousaf Khan, et al.
Published: (2022-09-01)

Evaluation of the Effects of Heteroaryl Ethylene Molecules in Combination with Antibiotics: A Preliminary Study on Control Strains
by: Carmelo Bonomo, et al.
Published: (2023-08-01)

Synthesis, anticancer activity and molecular docking of new quinolines, quinazolines and 1,2,4-triazoles with pyrido[2,3-d] pyrimidines
by: Ameen Ali Abu-Hashem, et al.
Published: (2024-03-01)

Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines
by: Irina P. Beletskaya, et al.
Published: (2013-02-01)

Hybrids of Imatinib with Quinoline: Synthesis, Antimyeloproliferative Activity Evaluation, and Molecular Docking
by: Carine Santos, et al.
Published: (2022-03-01)

Synthesis of 2-(6-substituted quinolin-4-yl)-1-(4-aryl-1H-1,2,3-triazol-1-yl) propan-2-ol as potential antifungal and antitubercular agents
by: Abhijit Shinde, et al.
Published: (2023-04-01)

Regioselectivity in the Thermal Rearrangement of Unsymmetrical 4-Methyl-4H-1,2,4-triazoles to 1-Methyl-1H-1,2,4-triazoles
by: Per H.J. Carlsen, et al.
Published: (2001-11-01)

New Quinoline-Based Heterocycles as Anticancer Agents Targeting Bcl-2
by: Rania Hamdy, et al.
Published: (2019-04-01)

Novel Triazole-Quinoline Derivatives as Selective Dual Binding Site Acetylcholinesterase Inhibitors
by: Susimaire P. Mantoani, et al.
Published: (2016-02-01)

9-(1H-Benzo[d]imidazol-2-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline
by: Gerardo García González, et al.
Published: (2017-03-01)

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts
by: Rodrigo Abonia, et al.
Published: (2019-03-01)

RuO4-mediated oxidation ofN-benzylated tertiary amines. Are amineN-oxides and iminium cations reaction intermediates?
by: Petride Horia, et al.
Published: (2004-06-01)

RuO4-mediated oxidation of N-benzylated tertiary amines. 3. Behavior of 1,4-dibenzylpiperazine and its oxygenated derivatives
by: Petride Horia, et al.
Published: (2006-12-01)

Synthesis of 2-azetidinones substituted quinoline derivative
by: Mashelkar Uday C., et al.
Published: (2013-01-01)

Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate
by: Wael Abdelgayed Ahmed Arafa, et al.
Published: (2019-06-01)

Recent Advances in the Synthesis of Bioactive Glycohybrids via Click-Chemistry
by: Kavita Singh, et al.
Published: (2023-08-01)

The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
by: Stefania Gambaro, et al.
Published: (2019-10-01)

α-Glucosidase and α-Amylase Inhibitory Potentials of Quinoline–1,3,4-oxadiazole Conjugates Bearing 1,2,3-Triazole with Antioxidant Activity, Kinetic Studies, and Computational Validation
by: Nosipho Cele, et al.
Published: (2022-08-01)

Quinoline as a probe molecule for determination of external Bronsted and Lewis acidity in zeolites /
by: 343391 Corma, A., et al.

Ag(I) Complexes of Imine Derivatives of Unexpected 2-Thiophenemethylamine Homo-Coupling and Bis-(<i>E</i>)-<i>N</i>-(furan-2-ylmethyl)-1-(quinolin-2-yl)methanimine
by: Adesola A. Adeleke, et al.
Published: (2021-06-01)

Synthesis, Structure–Activity Relationships, and Antiviral Profiling of 1-Heteroaryl-2-Alkoxyphenyl Analogs as Inhibitors of SARS-CoV-2 Replication
by: Dorothée Bardiot, et al.
Published: (2022-02-01)

The Synthesis, Antimicrobial Activity, and Molecular Docking of New 1, 2, 4-Triazole, 1, 2, 4-Triazepine, Quinoline, and Pyrimidine Scaffolds Condensed to Naturally Occurring Furochromones
by: Ameen Ali Abu-Hashem, et al.
Published: (2022-10-01)

Methyl 3-(Quinolin-2-yl)indolizine-1-carboxylate
by: Roumaissa Belguedj, et al.
Published: (2015-12-01)

5-Chloro-8-{[1-(2-chlorobenzyl)-1<em>H</em>-1,2,3-triazol-4-yl]methoxy}quinoline
by: Luz Karime Luna Parada, et al.
Published: (2018-12-01)

UV Properties and Loading into Liposomes of Quinoline Derivatives
by: Sara Battista, et al.
Published: (2021-05-01)

Recent Advances in Metal-Free Quinoline Synthesis
by: Ginelle A. Ramann, et al.
Published: (2016-07-01)

Glycoconjugation of Quinoline Derivatives Using the C-6 Position in Sugars as a Strategy for Improving the Selectivity and Cytotoxicity of Functionalized Compounds
by: Monika Domińska, et al.
Published: (2022-10-01)

Preparation of Quinoline-2,4-dione Functionalized 1,2,3-Triazol-4-ylmethanols, 1,2,3-Triazole-4-carbaldehydes and 1,2,3-Triazole-4-carboxylic Acids
by: David Milićević, et al.
Published: (2020-06-01)

Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
by: Branko Stanovnik, et al.
Published: (2012-05-01)

Novel 1,2,3-Triazole-Containing Quinoline–Benzimidazole Hybrids: Synthesis, Antiproliferative Activity, In Silico ADME Predictions, and Docking
by: Luka Krstulović, et al.
Published: (2023-10-01)