Toward Value-Added Chemicals from Carbohydrates via C–C Bond Cleavage and Coupling Transformations

ACS Catalysis, Год журнала: 2024, Номер 14(7), С. 5167 - 5197

Опубликована: Март 21, 2024

Renewable carbohydrates are nearly inexhaustible libraries of chemical building blocks, and significant research efforts have been devoted to their valorization valuable chemicals in the past decades. The commonly recognized main transformation routes include dehydration C–C bond cleavage pathways, which lead production conventional platform such as 5-hydroxymethylfurfural/furfural, lactic acid/lactates, so on. With huge availability on earth, other fine is very attractive but remains sparse. This Review therefore emphasizes utilization strategies based situ lower carbon fragments, glycolaldehyde erythrose, subsequent transformations, e.g. hydrogenation, hydrogenolysis, oxidation, nucleophilic addition, amination. isolation reactive intermediates avoided, leading formation a variety "unconventional" useful scaffolds, ethylene glycol, ethanol, keto-alcohols, glycolic acid, formic C4 skeleton α-hydroxy esters, N-containing compounds, etc. Inspired by active intermediates, direct conversion monosugars with similar structures through coupling furan-based also briefly reviewed. primary focus this show spectacular range that can be accessed from via approaches. A summary reviewed works some opportunities challenges within field underlined for future sugar chemistry.

Язык: Английский

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Advances in synthesis and biological activities of quinazoline scaffold analogues: A review

Arabian Journal of Chemistry, Год журнала: 2023, Номер 16(10), С. 105190 - 105190

Опубликована: Июль 28, 2023

Creating effective, ecologically friendly, and commercially viable synthetic routes is crucial in the design synthesis of organic substances. Quinazoline, a heterocyclic compound with nitrogen,is one most significant motifs diverse chemical reactivities many biological applications. Its derivatives comprise family fused heterocycles over 200 naturally occurring alkaloids. Over past few decades, newer, more complex drugs containing quinazolinone structures have been discovered, enormous progress designing various efficient protocols to construct these pharmacologically active scaffolds. This review evaluated recently investigated for synthesizing quinazolines their (from 2017-2023 till date). The current paper provides an up-to-date description recent advancements straightforward procedures that result creation quinazoline molecules. In addition, therapeutical activities numerous quinazoline-based were briefed assessed this review. We envisage information would assist researchers novel analogues as lead compounds.

Язык: Английский

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Visible-light photocatalyzed C–N bond activation of tertiary amines: a three-component approach to synthesize quinazolines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(6), С. 1245 - 1253

Опубликована: Янв. 1, 2024

A metal-free three-component approach has been developed to prepare 2,4-disubstituted quinazolines from

Язык: Английский

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A Systematic Review of Synthetic and Anticancer and Antimicrobial Activity of Quinazoline/Quinazolin‐4‐one Analogues

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

Abstract Quinazolines/quinazolin‐4‐ones are significant nitrogen‐containing heterocycles that exist in various natural products and synthetic scaffolds with diverse medicinal pharmacological applications. Researchers across the globe have explored numerous strategies to develop safer more potent quinazoline/quinazolinone analogues, particularly for combating cancer microbial infections. This review systematically examines scholarly efforts toward understanding this scaffold's pathways relevance, emphasizing role of metal non‐metal catalysts other reagents their synthesis. Additionally, article discusses selected compounds’ anticancer antimicrobial properties, a brief look into structure‐activity relationships.

Язык: Английский

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Metal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthon

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(12)

Опубликована: Фев. 10, 2023

Abstract Highly functionalized quinazolin‐4(3 H )‐ones were synthesized from reactions of N ‐aryl‐2‐aminobenzamides with trialkylamines under photocatalytic conditions by using eosin Y (EY) as a catalyst. The reaction proceeds mild in aqueous acetonitrile and has broad substrate scope. Mechanistic studies disclosed the electron‐donor nature intermediate 2,3‐dihydroquinazolin‐4(1 )‐one ( 3’ ) cycle to afford 2,3‐disubstituted‐quinazolin‐4(3 3 ). This methodology been extended synthesize benzo [4,5] imidazole[1,2‐ c ] quinazolines aa on large scale. Furthermore, synthesis potent central nervous system depressant (CNS) drug molecules such methaqualone la mecloqualone pa was also achieved successfully.

Язык: Английский

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Metal-Free N-Formylation of Amines Using Carbohydrates as C1 Synthon via C–C Bond Cleavage

Synthesis, Год журнала: 2024, Номер 56(09), С. 1449 - 1459

Опубликована: Янв. 10, 2024

Abstract Formamide group is an important part of many drug molecules, and herein a process for N-formylation amines using carbohydrates as the C1 synthon under oxidative metal-free reaction conditions has been reported first time. Literature syntheses formamides uses toxic, moisture sensitive costly reagents harsh conditions. Our formylation facile, economical, efficient broad substrate scope that led to synthesis thirty-three N-formylated compounds in excellent isolated yields.

Язык: Английский

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Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Май 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Язык: Английский

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Oxidative Cyclization of Trifluoroacetimidohydrazides with D‐Glucose for the Metal‐Free Synthesis of 3‐Trifluoromethyl‐1,2,4‐Triazoles

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(21), С. 4982 - 4987

Опубликована: Окт. 2, 2021

Abstract A metal‐free oxidative cyclization of readily available trifluoroacetimidohydrazides with D‐glucose for the assembly 3‐trifluoromethyl‐1,2,4‐triazoles has been disclosed. is applied as C1 synthon to provide methine source in reaction. Control experiments have conducted shed light on reaction mechanism. The synthetic utility protocol explored by implementation scale up and synthesis key skeleton NK I ‐receptor ligand. magnified image

Язык: Английский

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3-Phenylquinazolin-4(3H)-one via a renewable approach as an efficient corrosion inhibitor for mild steel in acid media

Materials Chemistry and Physics, Год журнала: 2023, Номер 308, С. 128238 - 128238

Опубликована: Июль 27, 2023

Язык: Английский

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Sustainable Synthesis of 2‐Hydroxymethylbenzimidazoles using D‐Fructose as a C₂ Synthon

Chemistry - An Asian Journal, Год журнала: 2021, Номер 16(22), С. 3754 - 3759

Опубликована: Сен. 22, 2021

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof concept was established synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) CH3CN at 90 °C for 1 h. The pivotal features this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and synthesis benzimidazole fused 1,4-oxazine. Control studies conventional synthons did not produce desired product, thus suggesting new reaction pathway from D-fructose.

Язык: Английский

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