Transition-metal-catalyzed synthesis of quinazolines: A review

Frontiers in Chemistry, Год журнала: 2023, Номер 11

Опубликована: Март 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.

Язык: Английский

---

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

Molecular Catalysis, Год журнала: 2023, Номер 542, С. 113110 - 113110

Опубликована: Апрель 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.

Язык: Английский

---

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

New Journal of Chemistry, Год журнала: 2023, Номер 47(17), С. 8268 - 8276

Опубликована: Янв. 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.

Язык: Английский

---

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

ChemCatChem, Год журнала: 2021, Номер 13(22), С. 4751 - 4758

Опубликована: Сен. 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.

Язык: Английский

---

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

Organometallics, Год журнала: 2022, Номер 41(11), С. 1314 - 1324

Опубликована: Май 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.

Язык: Английский

---

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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 5431 - 5439

Опубликована: Апрель 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.

Язык: Английский

---

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

Catalysis Science & Technology, Год журнала: 2023, Номер 13(11), С. 3358 - 3365

Опубликована: Янв. 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.

Язык: Английский

---

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

Synthesis, Год журнала: 2022, Номер 54(12), С. 2876 - 2884

Опубликована: Янв. 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.

Язык: Английский

---

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

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 16967 - 16977

Опубликована: Ноя. 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.

Язык: Английский

---

Synthesis of substituted quinazolines using Ru(II)-p-cymene catalysts containing ferrocene acylthiourea ligand via acceptorless dehydrogenative coupling

Inorganic Chemistry Communications, Год журнала: 2024, Номер 168, С. 112963 - 112963

Опубликована: Авг. 9, 2024

Язык: Английский

---