Transition-metal-catalyzed synthesis of quinazolines: A review

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

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

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

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Transition metal-free synthesis of 2-aryl quinazolines via alcohol dehydrogenation

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 542, P. 113110 - 113110

Published: April 6, 2023

We report here a transition metal-free synthesis of quinazoline derivatives starting from 2-aminobenzyl alcohols and aryl amides via an alcohol dehydrogenation strategy promoted by potassium tertiary butoxide. The control experiments are carried out to identify the reaction intermediates role K+ ion in reaction. DFT calculations unveil mechanism, with special focus on rate determining state. present method tolerates variety functional groups providing easy access diversely substituted quinazolines.

Language: Английский

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Highly Efficient and Recyclable Porous Organic Polymer Supported Iridium Catalysts for Dehydrogenation and Borrowing Hydrogen Reactions in Water

ChemCatChem, Journal Year: 2021, Volume and Issue: 13(22), P. 4751 - 4758

Published: Sept. 2, 2021

Abstract Benzothiazole‐doped porous organic polymers ( POP‐MBTS ) were synthesized from a copolymerization reaction of 2‐(6‐(4‐vinylphenyl)pyridin‐2‐yl)benzo[ d ]thiazole with divinylbenzene. The corresponding POP‐MBTS‐Ir was obtained and fully characterized using SEM, TEM, EDS, TGA, XPS, N 2 sorption isotherms, which disclosed that this catalyst has high surface area, hierarchical porosity, thermodynamic stability. Importantly, revealed catalytic activity for ten different kinds borrowing hydrogen dehydrogenation reactions in water good recovery performance. Furthermore, mechanistic investigations conducted the synthesis triazine derivatives.

Language: Английский

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NNO Pincer Ligand-Supported Palladium(II) Complexes: Direct Synthesis of Quinazolines via Acceptorless Double Dehydrogenative Coupling of Alcohols

Organometallics, Journal Year: 2022, Volume and Issue: 41(11), P. 1314 - 1324

Published: May 20, 2022

A sustainable approach for the synthesis of substituted quinazolines by sequential acceptorless dehydrogenative coupling 2-aminobenzyl alcohol with alcohols using new Pd(II)-NNO pincer-type complexes as catalysts was reported. Air-stable palladium(II) general formula [Pd(L)(PPh3)] (where L = 4-substituted methyl-2-pyrrolyl benzhydrazone ligands) were synthesized, and their compositions recognized analytical spectral methods (Fourier transform infrared (FT-IR), NMR, high-resolution mass spectrometry (HRMS)). Single-crystal X-ray crystallography confirmed tridentate coordination ligands existence square-planar geometry around metal ion. wide range quinazoline derivatives synthesized from double dehydrogenation benzyl 1.5 mol % catalyst loading a maximum 93% yield. The formation aminobenzaldehyde benzaldehyde intermediates via reaction control experiments.

Language: Английский

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Visible Light-Induced Decomposition of Acyl Peroxides Using Isocyanides: Synthesis of Heteroarenes by Radical Cascade Cyclization

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5431 - 5439

Published: April 24, 2023

Visible light-mediated facile synthesis of heteroarenes, namely, isoquinolines, benzothiazoles, and quinazolines, is demonstrated by employing isocyanides inexpensive acyl peroxides. It shown for the first time that singlet-excited decompose peroxides into aryl/alkyl radicals. The latter attack isocyanides, yielding imidoyl radicals subsequently cyclize to afford heteroarene products. protocol involving radical cascade reactions obviates requirement any external photocatalyst, oxidant, additive, base.

Language: Английский

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Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable synthesis of bis(indolyl)methanesviaacceptorless dehydrogenative coupling of alcohols

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(11), P. 3358 - 3365

Published: Jan. 1, 2023

New orthometallated Pd( ii ) C^N^S pincer catalyst-mediated sustainable and cost-effective synthesis of pharmacologically important bis(indolyl)methanes (23 examples up to 95% yield) via ADC is reported.

Language: Английский

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Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Synthesis, Journal Year: 2022, Volume and Issue: 54(12), P. 2876 - 2884

Published: Jan. 31, 2022

Abstract An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range substituted 2-aminobenzyl alcohols (hetero)aryl alkyl benzamides were well compatible to afford in excellent yields. Merits this new strategy are high atom-economy, mild conditions, simple operation, methodology is suitable a variety substrates.

Language: Английский

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Arene Ruthenium(II)-Catalyzed Sustainable Synthesis of 2,4-Disubstituted Quinazolines via Acceptorless Dual Dehydrogenative Coupling of Alcohols

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16967 - 16977

Published: Nov. 29, 2023

We demonstrate an efficient and sustainable strategy for the direct synthesis of 2,4-disubstituted quinazolines by arene Ru(II)benzhydrazone complex via eco-friendly sequential acceptorless dehydrogenative coupling 2-aminobenzhydrol derivatives benzyl alcohols first time. The new ruthenium(II) general formula [(η6-p-cymene)Ru(L1)Cl] (L1-acenaphthenequinone hydrazone) has been synthesized characterized analytical, spectroscopic, single-crystal X-ray diffraction techniques. A broad spectrum have successfully derived (25 examples) from with various using 1 mol % catalyst loading in presence NH4OAc. present protocol is highly selective produces a maximum yield 95% under mild reaction conditions. different intermediates detected through control experiments such as aldehyde, 2-aminobenzophenone, benzylidene(amino)phenylmethanone, 1,2-dihydroquinazoline are isolated authenticated NMR study. Gratifyingly, simple atom economic release water hydrogen gas only byproducts. gram-scale 2-(4-methoxyphenyl)-4-phenylquinazoline illustrates synthetic utility protocol.

Language: Английский

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Cucurbit[6]uril supported β-Ni(OH)₂ nanoparticles as a heterogeneous catalyst for the synthesis of quinazolines via acceptorless dehydrogenative coupling of alcohols with nitriles

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(44), P. 21356 - 21365

Published: Jan. 1, 2022

Synthesis of a series quinazolines using β-Ni(OH) 2 -CB[6] as heterogeneous nanocatalyst.

Language: Английский

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