[BPy][OH] Immobilized Hydrotalcite Clay Catalytic System for 1,2-dihyd-roquinazolines Synthesis DOI
Vivek Srivastava

Current Organocatalysis, Journal Year: 2023, Volume and Issue: 11(1), P. 33 - 43

Published: July 27, 2023

Abstract: We easily synthesized two ionic liquids, [BMIM][OH] and [BPy][OH], with high yield. found that hydrotalcite clay, mediated by these is a highly effective catalyst for synthesizing biologically active 1,2-dihydroquinazoline derivatives. Using simple reaction protocol easy product isolation steps, we successfully 18 different derivatives were able to recycle the catalysts up 8 times. Overall, use of [BPy][OH] provide more efficient environmentally friendly method quinazolines compared traditional methods often require harsh conditions toxic reagents. Background: 1,2-Dihydroquinazolines are an important class heterocyclic compounds diverse biological activities, including anticancer, antifungal, antibacterial properties. They also exhibit other pharmacological activities such as antihypertensive, anti-inflammatory, antiviral effects. The synthesis 1,2-dihydroquinazolines dates early 20th century when they first Pictet Huber in 1911 condensation anthranilic acid aldehydes or ketones presence strong acids. Since then, numerous have been developed their synthesis, cyclization o-aminobenzamides, o-aminoaryl ketones, Lewis acids transition metals. In recent years, development new synthetic selective has great interest chemists, particularly pharmaceutical industry. These include microwave irradiation, ultrasound, liquids green solvents. : area research, continue be improve properties various applications. Methods: yields. Results: our results insights into sustainable 1, 2-dihydroquinazolines. Conclusion: summary, studies demonstrated liquid clay catalytic system could used 2-dihydroquinazolines using aromatic carbonyl compounds, amino benzophenone derivatives, aldehydes. electron-donating substituents phenyl group provided higher yields than electron-withdrawing groups, para position aldehyde had significant effect ortho meta position. Our was recyclable eight runs without loss activity.

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

38
Ruthenium pincer complex catalyzed efficient synthesis of quinoline, 2-styrylquinoline and quinazoline derivatives via acceptorless dehydrogenative coupling reactions DOI

Dipanjan Bhattacharyya,

Priyanka Adhikari,

Kritartha Deori

et al.

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(18), P. 5695 - 5702

Published: Jan. 1, 2022

The synthesis of N-heterocycles has been considered an emerging area chemical research due to their extensive utilization in pharmaceuticals, materials science, and natural product synthesis.

Language: Английский

Citations

36
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

17
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
Facile synthesis of quinolines and N-alkylation reactions catalyzed by ruthenium(II) pincer type complexes: Reaction mechanism and evidences for ruthenium hydride intermediate DOI
Sain Singh, Angshuman Roy Choudhury, Kaushik Ghosh

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 549, P. 113424 - 113424

Published: Aug. 19, 2023

Language: Английский

Citations

10
A Metal‐Free KOtBu‐Mediated Protocol towards the Synthesis of Quinolines, Indenoquinolines and Acridines DOI

Pendyala Satya Kishore,

Raghuram Gujjarappa, Mayur Jagdishbhai Patel

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(4)

Published: Jan. 23, 2024

Abstract An expeditious strategy has been developed for the synthesis of diverse quinolines, indenoquinolines and acridines using KO t Bu‐mediated reaction conditions. The designed process utilizes 2‐aminoaryl carbaldehydes/2‐aminoaryl ketones methyl/methylene group containing as readily available feedstock. chemical transformation was affected at room temperature within a short duration time to obtain N ‐heterocycles yields up 92 %. established also exhibits considerable functional tolerance with an operational simplicity.

Language: Английский

Citations

3
Efficient Synthesis of Benzimidazole and Quinoline Derivatives Catalyzed by Functionalized Amidato Ruthenium Complexes in Water via Acceptorless Dehydrogenative Coupling Strategy DOI
Xin Liu, Wenzhe Dong, Yining Liu

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(16)

Published: July 10, 2023

Abstract Transition‐metal‐catalyzed acceptorless dehydrogenative coupling (ADC) has emerged as a sustainable synthetic strategy for the construction of N ‐heteroaromatics. Herein, series water‐soluble amidato Ru catalysts were designed, synthesized, and utilized in selective synthesis 2‐substituted benzimidazoles from aromatic diamines primary alcohols, well quinolines substituted 2‐aminobenzyl alcohols acetophenones via ADC water. Catalyst 1 d bearing strong electron‐donating hydroxyl group on ligand exhibited best catalytic activity. The system demonstrated remarkable efficiency versatility, allowing application over 40 substrates two reactions with good to high yields. Based control experiments density functional theory (DFT) calculations, plausible mechanism was proposed, highlighting significant role functionalized complexes catalyzing alcohol dehydrogenation an outer‐sphere pathway.

Language: Английский

Citations

6
One‐Pot Synthesis of Quinazolines via Elemental Sulfur‐Mediated Oxidative Condensation of Nitriles and 2‐(Aminomethyl)anilines DOI
Yu‐Xing Tan, Wujiu Jiang, Penghui Ni

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3600 - 3606

Published: July 27, 2022

Abstract A strategy for the synthesis of quinazolines via elemental sulfur‐mediated oxidative condensation nitriles and 2‐(aminomethyl)anilines was developed. The reaction carried out under metal‐/solvent‐free conditions, tolerates a wide range functional groups to provide corresponding products in 56%‐91% yield, can be performed on gram‐scale. UV/Vis absorption fluorescence spectra several product derivatives were measured study their photophysical properties. magnified image

Language: Английский

Citations

10
Electrochemical Oxidation Decarboxylative Cyclization of α-Keto Acid with o-Aminobenzylamine DOI
Jiwei Wu, Jun He, Jingjing Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 972 - 972

Published: Jan. 1, 2024

Language: Английский

Citations

1
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