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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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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Design, synthesis and photophysical properties of novel 2,4-disubstituted quinazolines

Journal of Photochemistry and Photobiology A Chemistry, Год журнала: 2025, Номер unknown, С. 116390 - 116390

Опубликована: Март 1, 2025

Язык: Английский

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One Pot Synthesis and Mechanistic Insights of Quinazoline and related molecules

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134635 - 134635

Опубликована: Март 1, 2025

Язык: Английский

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Catalytic Asymmetric Approach to 1,3,4,5‐Tetrahydro‐1,4‐benzodiazepin‐2‐ones in One‐Pot

ChemCatChem, Год журнала: 2024, Номер 16(16)

Опубликована: Апрель 3, 2024

Abstract Herein we illustrate a first asymmetric synthesis of medicinally attractive tetrahydro‐1,4‐benzodiazepin‐2‐ones performed under catalytic conditions and one‐pot fashion. The process relies on sequential Knoevenagel reaction/asymmetric epoxidation/domino ring‐opening cyclization (DROC) using commercially available aldehydes, phenylsulfonylacetonitrile, cumyl hydroperoxide, 2‐(aminomethyl)aniline readily quinine‐derived urea as the catalyst. heterocycles have been isolated with good regioselectivity, satisfactory to yield up 98 % ee. protocol proved also be suitable for preparation previously undescribed 1,5‐dihydro‐4,1‐benzoxazepin‐3(2H)‐ones 86

Язык: Английский

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Electrochemical Oxidation Decarboxylative Cyclization of α-Keto Acid with o-Aminobenzylamine

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(3), С. 972 - 972

Опубликована: Янв. 1, 2024

Язык: Английский

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Pragmatic Access to Hybrid Quinoxaline Scaffold Mediated by Elemental Sulfur Enabling Actualization to π-Extended and Aza-Annulated Heterocyclic Units

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 27, 2024

A metal-free approach for synthesizing hybrid quinoxaline derivatives from sulfoxonium ylide and a 1,5-bis-nucleophilic N-heterocycle mediated by elemental sulfur is presented to illuminate the [5+1] cascade cyclization sequence. Large-scale synthesis postsynthetic functionalizations annulative π-extension intramolecular aza-annulation reactions reveal potential utility actualize fabricated approach.

Язык: Английский

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Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation

New Journal of Chemistry, Год журнала: 2023, Номер 47(19), С. 9377 - 9382

Опубликована: Янв. 1, 2023

We report a Cu( i )-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation by using acetamide as nitrogen source and H 2 O hydrogen source.

Язык: Английский

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Electrochemical Synthesis of Quinazolines: N–H/C(sp³)–H Coupling of o-Carbonyl Anilines with Amino Acids and Amines

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 11, 2024

A mild and efficient electrochemical protocol for the synthesis of quinazolines through N-H/C(sp

Язык: Английский

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TFA-Catalyzed cascade annulation of thioamides with aromatic hydrazides/amines: an internal oxidant-triggered protocol to diverse N-heterocycles

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 1, 2024

Язык: Английский

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