Synthesis and catalytic activity of POCOP ruthenium(II) and iron(II) pincer complexes derived from 1,3- and 1,7-dihydroxynaphthalenes DOI

Juan Carlos Temich-Escribano,

Manuel Alejandro Roque Ramires,

Samanta Ortiz-Rojas

et al.

Journal of Coordination Chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 17

Published: Dec. 31, 2024

Ruthenium(II) and iron(II) POCOP pincer complexes have readily been obtained from ligands derived the 1,3- 1,7-dihydroxynaphtalene isomers. The two ruthenium(II) isomers displayed remarkable catalytic activity for Friedländer annulation, reaction was tolerant to a wide array of electron-withdrawing -donating substituted ketones. reactions produced selectively quinoline derivatives in conversions up 99% at low catalysts loadings with turnover numbers close 1000. iron also exhibited notable activity, albeit lower than their ruthenium counterparts. These results mark significant advancement developing derivatives.

Language: Английский

Single-Atom Fe-Catalyzed Acceptorless Dehydrogenative Coupling to Quinolines DOI

Yanze Lu,

Zhu Meiling,

Sanxia Chen

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(33), P. 23338 - 23347

Published: Aug. 6, 2024

A single-atom iron catalyst was found to exhibit exceptional reactivity in acceptorless dehydrogenative coupling for quinoline synthesis, outperforming known homogeneous and nanocatalyst systems. Detailed characterizations, including aberration-corrected HAADF-STEM, XANES, EXAFS, jointly confirmed the presence of atomically dispersed centers. Various functionalized quinolines were efficiently synthesized from different amino alcohols a range ketones or alcohols. The achieved turnover number (TON) up 10

Language: Английский

Citations

12
Expanding the library of β-ketoiminates via terminal alkylation of the backbone and their application to the synthesis of unsymmetric 2,4-disubstituted quinolines DOI
Xu Zhu, Zihan Kang,

Chunxi Chen

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: 172, P. 134463 - 134463

Published: Jan. 7, 2025

Language: Английский

Citations

0
Ruthenium(II)-Catalyzed Synthesis of N-Heterocycles via Ac-ceptorless Dehydrogenative Condensation DOI
Chong Zhang, Bowen Hu, Dafa Chen

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 1029, P. 123545 - 123545

Published: Jan. 31, 2025

Language: Английский

Citations

0
Recent Advances in the Synthesis of Quinolines: A Focus on Oxidative Annulation Strategies DOI Open Access

Mao-Lin Liao,

Peng-Peng Liu,

Jiacheng Yang

et al.

Catalysts, Journal Year: 2025, Volume and Issue: 15(5), P. 441 - 441

Published: April 30, 2025

Quinoline, a heterocyclic scaffold of paramount importance in medicinal and industrial chemistry, has garnered significant attention due to its versatile application. Traditional synthetic methods, dating back over century, have evolved into innovative strategies leveraging catalytic C–H bond activation, transition-metal-free protocols, photo-induced oxidative cyclization. Recent advancements highlight the synergistic roles catalysts, oxidants, solvents enhancing molecular reactivity reaction efficiency. This review systematically summarizes state-of-the-art annulation techniques for quinoline synthesis, emphasizing mechanistic insights practical applications.

Language: Английский

Citations

0
Iron‐Catalyzed Transfer Hydrogenation: Divergent Synthesis of Quinolines and Quinolones from ortho‐Nitrobenzyl Alcohols DOI
Simin Chun,

Ramachandra Reddy Putta,

Junhwa Hong

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(19), P. 3367 - 3374

Published: Aug. 17, 2023

Abstract Herein, we report the divergent synthesis of quinolines and quinolones via a transfer hydrogenative condensation ortho ‐nitrobenzyl alcohols in one step. The reaction proceeded using cyclopentadienone iron complex without any additional redox reagents. After hydrogenation between secondary alcohols, subsequent Friedländer annulation affords polysubstituted quinoline products 22–90% (39 examples). developed method was also applied to synthesize by primary instead (12 obtained were converted into several drug candidates demonstrate its synthetic potential.

Language: Английский

Citations

9
Using Quinolin-4-Ones as Convenient Common Precursors for a Metal-Free Total Synthesis of Both Dubamine and Graveoline Alkaloids and Diverse Structural Analogues DOI Creative Commons
Rodrigo Abonı́a,

Lorena Cabrera,

Diana Arteaga

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(9), P. 1959 - 1959

Published: April 25, 2024

The Rutaceae family is one of the most studied plant families due to large number alkaloids isolated from them with outstanding biological properties, among quinoline-based Graveoline 1 and Dubamine 2. common methods for synthesis 2 their derivatives involves cycloaddition reactions or metal-catalyzed coupling processes but some limitations in scope functionalization quinoline moiety. As a continuation our current studies on chemical transformation 2-aminochalcones, we are reporting here an efficient metal-free approach total along analogues structural diversity, through two-step sequence involving intramolecular cyclization, oxidation/aromatization, N-methylation oxidative C-C bond processes, starting dihydroquinolin-4-ones as precursors construction structures both classes alkaloids.

Language: Английский

Citations

3
Lewis Acid‐Promoted Domino Processes for the Synthesis of Homoallylic Amines, Quinolines and Tetrahydroquinolines DOI
Rahul Vishwakarma, Nagaraju Vodnala, Dulal Musib

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 3010 - 3021

Published: May 1, 2024

Abstract Herein, the synthesis of homoallylic amines, quinolines, and tetrahydroquinolines has been demonstrated. The domino one‐pot multi‐component approach accomplished using Lewis acid‐catalyzed conditions. A useful scaffold construction strategy can be achieved by controlling electronic effect aniline rather than relying on reaction described method applies to a wide variety substrates embedded with diverse functional groups extended toward natural products. Suitable control experiments, real‐time NMR studies, DFT calculations have validated reported process. protocol outlines for synthesizing amines controlled properties anilines.

Language: Английский

Citations

3
Dinuclear Ru(II) Schiff Base Complex Catalyzed One-Pot Synthesis of Quinolines through Acceptorless Dehydrogenative Coupling of Secondary Alcohols with 2-Nitrobenzyl Alcohol DOI
Gopal Deshmukh, Santosh J. Gharpure, Ramaswamy Murugavel

et al.

Organometallics, Journal Year: 2024, Volume and Issue: 43(10), P. 1190 - 1202

Published: May 10, 2024

Dinuclear Ru(II) complexes [(p-cymene)2(RuCl)2L1]2X (X = BF4 (Ru1); X PF6 (Ru2)) and mononuclear [(p-cymene)(RuCl)L2]BF4 (Ru3) (where L1 N,N′-(3,3′,5,5′-tetraisopropyl-[1,1′-biphenyl]-4,4′-diyl)bis(1-(pyridin-2-yl)methanimine); L2 N-(2,6-diisopropyl-phenyl)-1-(pyridin-2-yl)-methanimine) have been synthesized characterized by spectroscopic analytical techniques. Ru1 Ru2 orchestrate direct transformation of 2-nitrobenzyl alcohols to quinolines under mild conditions with significant efficiency even when employed at a minimal catalyst loading 0.1 mol %. Proportional experiments carried out the corresponding complex Ru3 keeping Ru content same (0.2 % Ru3) reveal superior activity bimetallic system for one-pot quinoline synthesis. Late-stage functionalization bioactive steroids scale-up synthesis demonstrate practical applicability present system. A probable mechanism this conversion is proposed based on trapping many intermediates ESI-mass spectroscopy. These mechanistic studies further substantiated ReactIR monitoring progress reaction in real time.

Language: Английский

Citations

3
Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives DOI

Krishna Prasad Gnyawali,

Aldiyar Shakenov,

Pandula T. Kirinde Arachchige

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11119 - 11135

Published: July 26, 2024

The catalytic system generated in situ from the cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 2,3,4,5-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for promoting deaminative coupling reaction of 2-aminoaryl aldehydes branched amines form 2-substituted quinoline products. analogous ketones led regioselective formation 2,4-disubstituted A number biologically active derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using method.

Language: Английский

Citations

3
Molybdenum Catalyzed Acceptorless Dehydrogenation of Alcohols for the Synthesis of Quinolines DOI Creative Commons
Beatriz García, Beatriz Royo

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(15)

Published: Feb. 23, 2024

Abstract The first molybdenum triazolylidene complexes catalyzing the atom‐economical synthesis of quinolines through acceptorless dehydrogenative coupling alcohols is reported. A new family Mo(0) bearing chelating bis‐1,2,3‐triazolylidene, pyridyl‐1,2,3‐triazolylidene, and bis‐triazole ligands have been prepared applied as catalysts for quinolines. Interestingly, Mo bis‐1,2,3‐triazolylidene with alkyl groups (Et, n ‐Bu) displayed superior catalytic activities than those containing aryl substituents on rings. Control experiments corroborated that reaction involves dehydrogenation pathway.

Language: Английский

Citations

2