Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities DOI Creative Commons

Hongling Shui,

Yuhong Zhong, Renshi Luo

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 18, P. 1507 - 1517

Published: Oct. 27, 2022

The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols aryl/heteroaryl/alkyl secondary in one pot via a cyclometalated iridium-catalyzed ADC reaction. This has some advantages, such as easy availability of raw materials, mild conditions, wide range substrates, environmental friendliness which conforms to the principles green chemistry. Furthermore, gram-scale experiment with low catalyst loading offers potential access aryl/heteroaryl quinolones suitable amounts. addition, antibacterial antifungal activities evaluated vitro, experimental results showed that compounds 3ab, 3ad, 3ah against Gram-positive bacteria compound 3ck C. albicans better than reference drug norfloxacin.

Language: Английский

Dehydrogenative Synthesis of Quinolines and Quinazolines via Ligand-Free Cobalt-Catalyzed Cyclization of 2-Aminoaryl Alcohols with Ketones or Nitriles DOI
Zhiqiang Hao, Xiaoyu Zhou, Zongwen Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 12596 - 12607

Published: Sept. 26, 2022

We present a convenient and efficient protocol to synthesize quinolines quinazolines in one pot under mild conditions. A variety of substituted were synthesized good excellent yields (up 97% yield) from the dehydrogenative cyclizations 2-aminoaryl alcohols ketones catalyzed by readily available Co(OAc)2·4H2O. This cobalt catalytic system also showed high activity reactions 2-aminobenzyl with nitriles, affording various quinazoline derivatives 95% yield). The offers an environmentally benign approach for synthesis N-heterocycles employing earth-abundant salt ligand-free

Language: Английский

Citations

39
Transition-metal-catalyzed synthesis of quinazolines: A review DOI Creative Commons
T. N. Rekha,

Seok‐Ho Kim,

Dongyun Shin

et al.

Frontiers in Chemistry, Journal Year: 2023, Volume and Issue: 11

Published: March 16, 2023

Quinazolines are a class of nitrogen-containing heterocyclic compounds with broad-spectrum pharmacological activities. Transition-metal-catalyzed reactions have emerged as reliable and indispensable tools for the synthesis pharmaceuticals. These provide new entries into pharmaceutical ingredients continuously increasing complexity, catalysis these metals has streamlined several marketed drugs. The last few decades witnessed tremendous outburst transition-metal-catalyzed construction quinazoline scaffolds. In this review, progress achieved in quinazolines under transition metal-catalyzed conditions summarized reports from 2010 to date covered. This is presented along mechanistic insights each representative methodology. advantages, limitations, future perspectives through such also discussed.

Language: Английский

Citations

18
A sustainable approach for nickel nanoparticles synthesis: expeditious access to N-heterocycles under heterogeneous condition and photophysical studies DOI

R. Thrilokraj,

Rajeev V. Hegde, Arnab Ghosh

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(17), P. 8268 - 8276

Published: Jan. 1, 2023

A sustainable and environmentally benign biogenic technique for one-step synthesis of Ni-NPs (NiC 2 O 4 ·2H O-NPs) using Portulaca oleracea (purslane) leaf extract has been disclosed the first time.

Language: Английский

Citations

15
Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles DOI
Fatemeh Doraghi,

Farzad Gilaninezhad,

Somaye Karimian

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

Citations

4
Recent Developments of Transition‐Metal‐Catalyzed Cross‐Coupling of Nitriles and Alcohols DOI
Xiuju Cai,

Xurui Wei,

Ming Huang

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(32)

Published: Aug. 22, 2024

Abstract Cross‐coupling of nitriles and alcohols offers an environmentally friendly atom‐economical method for the synthesis various valuable compounds. These compounds include α ‐alkylated ‐olefinated nitriles, primary amines, imines, N ‐alkylation amides, ‐heterocycles, δ ‐hydroxynitriles, olefins, etc . Herein, we have reviewed recent developments (from 2013–date) transition‐metal‐catalyzed cross‐coupling alcohols. A number transition metal complexes such as noble metals Ru Ir, well base Mn, Fe, Co, Ni are presented. Moreover, different product types, reaction conditions mechanisms discussed to understand catalyst development.

Language: Английский

Citations

4
Synthesis and structural characterization of palladium pincer complexes: Sustainable synthesis of benzothiazoles DOI
Pennamuthiriyan Anandaraj, S. Saranya, Rengan Ramesh

et al.

Applied Organometallic Chemistry, Journal Year: 2023, Volume and Issue: 37(5)

Published: Feb. 27, 2023

An efficient Pd(II)N^N^S pincer type catalysts‐promoted sustainable construction of pharmaceutically important benzothiazole derivatives from primary alcohols and 2‐aminothiophenol via acceptorless dehydrogenative coupling (ADC) method has been described. The newly synthesized ligand L 2 the Pd(II) complexes in addition to 1 3 were characterized by analytical Fourier transform infrared spectroscopy (FT‐IR), UV–visible (UV–vis), nuclear magnetic resonance (NMR) spectral techniques. Further, ORTEP views established a single crystal XRD study, which evidenced coordination thiosemicarbazone ligands disclose square‐planar geometry around ion. present homogeneous catalytic system involves synthesizing range benzothiazoles C−S C−N bond formation with excellent yields up 93%. described methodology employs sustainable, highly abundant, inexpensive alcohol as starting material using mol% catalyst loading, water hydrogen gas are only by‐products. Furthermore, plausible mechanism involving situ aldehyde dehydrogenation proposed. A large‐scale synthesis 2‐(4‐methoxyphenyl)benzo[d]thiazole illustrates synthetic utility protocol.

Language: Английский

Citations

7
Facile Synthesis of 2-Substituted Quinazolines via Ruthenium(II)-Catalyzed Acceptorless Dehydrogenative Coupling DOI

Shulei Wu,

Qianqian Lei,

Zaoduan Wu

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(4), P. 305 - 318

Published: Feb. 1, 2024

Abstract:: This study aims to develop a practical and facile one-pot synthesis of 2- substituted quinazolines. Using commercially available structurally simple ruthenium( II) complex as the catalyst synthesize series quinazoline derivatives via acceptorless dehydrogenative coupling. The mechanism this reaction was explored by control DFT calculation. protocol offers access diverse array (52 examples) in moderate excellent yields (29%-98%). In summary, we have developed an efficient ruthenium (II)-catalyzed ADC under air atmosphere. only produces hydrogen water by-products, serving sustainable atom-efficient synthetic approach.

Language: Английский

Citations

1
Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium DOI Creative Commons
Dāgs Dāvis Līpiņš,

Andris Jeminejs,

Una Ušacka

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 675 - 683

Published: March 28, 2024

2-Chloro-4-sulfonylquinazolines undergo functional group swap when treated with an azide nucleophile: 1) the replaces sulfonyl at C4 position; 2) intrinsic azide–tetrazole tautomeric equilibrium directs nucleofugal sulfinate from first step to replace chloride C2 position. This transformation is effective quinazolines bearing electron-rich substituents. Therefore, title transformations are demonstrated on 6,7-dimethoxyquinazoline core, which present in pharmaceutically active substances. The methodology application showcased by transforming obtained 4-azido-6,7-dimethoxy-2-sulfonylquinazolines into α 1 -adrenoceptor blockers terazosin and prazosin further C2-selective S N Ar reaction reduction.

Language: Английский

Citations

1
The Catalysts-Based Synthetic Approaches to Quinolines: A Review DOI

Shrishti Tripathi,

Rajnish Kumar, Avijit Mazumder

et al.

Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 20(10), P. 921 - 937

Published: June 26, 2024

The most common heterocyclic aromatic molecule with potential uses in industry and medicine is quinoline. Its chemical formula C9H7N, it has a distinctive double-ring structure pyridine moiety fused benzene ring. Various synthetic approaches synthesize quinoline derivatives. These include solvent-free approach, mechanochemistry, ultrasonic, photolytic microwave catalytic approaches. One of the important catalyst-based approach which different catalysts are used such as silver-based catalysts, titanium-based nanoparticle new iridium barium-based iron-based gold-based nickel-based catalyst, some metal-based photocatalyst, α-amylase biocatalyst, by using multifunctional metal-organic framework-metal tandem catalyst etc. In present study, we summarized catalyst-promoted reactions that have been reported for synthesis Hopefully, study will be helpful researchers.

Language: Английский

Citations

0
Facile Synthesis of New Antiviral Fluoro-Quinazolines Enabled by Merging Domino Reactions DOI
Svetlana B. Tsogoeva,

Sascha Kohlbauer,

Honglin Xia

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

Abstract Quinazolines, particularly fluoro-quinazolines, represent important structural motifs in bioactive molecules and pharmaceuticals. Despite several known synthetic routes, the efficient synthesis of fluorine-containing quinazolines remains a challenge. Herein, straightforward sustainable fluorine-substituted using domino sequences is reported. The obtained novel fluoro-quinazoline compounds exhibit significant vitro activity against human cytomegalovirus (HCMV), expanding library potential antiviral drug compounds. Our finding outlays toolkit for fluoro-quinazolines introduces new agents HCMV therapy.

Language: Английский

Citations

0