DBU-catalyzed annulation strategy for modular assembly of 2,3-difunctionalized dihydrobenzofurans

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An organocatalytic approach for the construction of 2,3-dihydrobenzofuran scaffold through a formal [4 + 1] annulation 2-(2-nitrovinyl)phenols and α-bromoacetophenones in presence 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been developed. This protocol could be easily performed one mmol scale, giving broad range derivatives moderate to excellent yields remarkable diastereoselectivity (>20 : 1 dr general) with good functional group tolerance.

Language: Английский

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Base‐Mediated [4+1] Annulation Strategy for Modular Assembly of Alkynyl/Carboxylated Dihydrobenzofurans

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

Abstract An efficient and operational [4+1] annulation strategy toward functional dihydrobenzofurans from 2‐bromomalonates in situ generated alkynyl o ‐quinone methides (from ‐hydroxyphenyl propargylamines) has been developed. Without the need for pre‐dried solvent inert atmosphere protection, a broad range of substituted propargylamines are well‐tolerated, producing expected alkynyl/carboxylated with good to high yields. Furthermore, gram‐scale synthesis valuable alkenyl/carboxylated construction were conducted provide great potential value medicinal chemistry other related disciplines.

Language: Английский

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

Processes, Journal Year: 2025, Volume and Issue: 13(4), P. 1038 - 1038

Published: March 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.

Language: Английский

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Baeyer–Villiger oxidation: a promising tool for the synthesis of natural products: a review

RSC Advances, Journal Year: 2024, Volume and Issue: 14(32), P. 23423 - 23458

Published: Jan. 1, 2024

Baeyer-Villiger oxidation is a well-known reaction utilized for the synthesis of lactones and ester functionalities from ketones. Chiral can be synthesized chiral or racemic ketones by employing asymmetric oxidation. These act as key intermediates in most biologically active natural products, their analogues, derivatives. Various monooxygenases oxidizing agents facilitate BV oxidation, providing broad range synthetic applications organic chemistry. The variety enzymatic chemoselective oxidations substantial role products i.e., alkaloids, polyketides, fatty acids, terpenoids, etc. (reported since 2018) have been summarized this review article.

Language: Английский

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A Review: Recent Advances in Chemistry and Applications of 2,4-Dihydroxybenzaldehyde Oxime and Its Transition Metal Complexes

Journal of Advanced Chemical Sciences, Journal Year: 2024, Volume and Issue: 10(4), P. 808 - 812

Published: Nov. 24, 2024

This review presents a comprehensive overview of the recent advances in chemistry and applications 2,4-dihydroxybenzaldehyde oxime (DHBO) its transition metal complexes. DHBO, characterized by unique hydroxyl functional groups, has gained significant attention due to versatile reactivity potential across various fields, including pharmaceuticals, catalysis, environmental science. Recent synthetic methodologies, microwave-assisted techniques green approaches, have improved efficiency sustainability DHBO production. The formation complexes with been focal point research, revealing enhanced catalytic properties biological activities compared free ligand. These shown promise organic synthesis, particularly oxidation reduction reactions, as well drug development, exhibiting antimicrobial anticancer properties. Furthermore, remediation, removing heavy metals pollutants, underscores their significance addressing contemporary challenges. also provides current knowledge on characterization, complexes, highlighting importance both academic research industrial applications. By elucidating multifaceted roles this work aims pave way for future innovation promising area study.

Language: Английский

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Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Dec. 13, 2024

2,3-Dihydrobenzofurans are noteworthy scaffolds in organic and medicinal chemistry, constituting the structural framework of many varied medicinally active compounds. Moreover, a diverse variety biologically potent natural products also contain this heterocyclic nucleus. Reflecting on wide biological substantiality dihydrobenzofurans, several innovative facile synthetic developments evolving to achieve these heterocycles. This review summarizes transition-metal-free, efficient, novel pathways toward constructing dihydrobenzofuran nucleus established after 2020.

Language: Английский

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