Base-Promoted [4 + 1 + 1] Multicomponent Tandem Cycloaddition of Ortho-Substituted Nitroarenes, Aldehydes, and Ammonium Salts To Access 2,4-Substituted Quinazoline Frameworks

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(5), С. 1982 - 1995

Опубликована: Янв. 23, 2025

We report a base-promoted, metal-free multicomponent tandem reaction, involving [4 + 1 1] cycloaddition process between ortho-substituted nitroarenes, aldehydes, and ammonium salts. Modifying the substituents on nitroaromatic compounds effectively provides structurally diverse 2-substituted 4-alkenylquinazolines with good to excellent yields (77%-90% quinazoline 51 examples) high tolerance for various inorganic salts (13 examples, such as NH3·H2O, NH4Cl, NH4HF2). A new method constructing 2,4-substituted selectivity from simple nitrogen source was developed, reaction can be scaled up gram scale. Additionally, this also facilitates preparation of organic molecules photophysical properties, offering insights into further transformation quinazolines.

Язык: Английский

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Synthesis of 2,3-Dihydrobenzofuran Chalcogenides Under Visible Light: A Sustainable Approach

Processes, Год журнала: 2025, Номер 13(4), С. 1038 - 1038

Опубликована: Март 31, 2025

This study introduces a visible light-mediated synthesis of 2,3-chalcogenil-dihydrobenzofuran through the oxyselenocyclization 2-allylphenols in presence chalcogenides. Emphasizing sustainability, this method is notably enhanced by proceeding under mild conditions, facilitated straightforward I2/SnCl2 as promoter and blue LED irradiation to activate process. A variety functional groups were effectively tolerated our developed approach, leading desired products with yields ranging from good excellent, demonstrating way versatility method. In addition, synthesized compounds characterized using 1H 13C NMR techniques.

Язык: Английский

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Photocatalytic synthesis of carbamoylated chroman-4-ones via radical cascade cyclization of 2-(allyloxy)arylaldehydes and oxamic acids

Molecular Catalysis, Год журнала: 2025, Номер 582, С. 115168 - 115168

Опубликована: Май 2, 2025

Язык: Английский

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Syntheses of 2,4‐Substituted Quinazolines via One‐Pot Three‐Component Reactions Based on Manganese Dioxide/tert‐Butyl Hydrogen Peroxide Co‐Oxidation Using Alcohols

Journal of Heterocyclic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 25, 2024

ABSTRACT Quinazolines and their derivatives occur in various natural products pharmaceuticals, thus, methods of synthesizing quinazolines have been explored. They traditionally synthesized via two‐component reactions, but these strategies often suffer from the unavailability starting materials limited substrate scopes. To overcome problems, three‐component reactions using additional N sources were developed. Aldehydes initially used alcohols are greener less toxic than aldehydes. However, previously reported involving use require utilization transition metal catalysts, ultrahigh temperatures, extended durations. Thus, an efficient, practical method alcohol is desirable. A facile one‐pot utilizing alcohols, 2‐aminobenzoketones, ammonium acetate for first time, active MnO 2 tert ‐butyl hydrogen peroxide (TBHP) as synergistic oxidants. TBHP play dual roles: First, they oxidize to aldehyde then facilitate transformation intermediate into product. During oxidation, effect particularly evident. The aldehydes generated situ oxidation undergo immediate subsequent thereby minimizing volatilization side such polymerization.

Язык: Английский

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Synthesis of 2-arylquinazolines by Chan–Evans–Lam coupling of 2-formylphenylboronic acids with amidines

Chemistry of Heterocyclic Compounds, Год журнала: 2024, Номер 60(3-4), С. 169 - 174

Опубликована: Апрель 1, 2024

Язык: Английский

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