European Journal of Organic Chemistry最新文献

The Front Cover shows a calm night sky filled with molecular constellations—gem-difluorinated fused bicyclic amines. At the center, a radiant CF₂ fragment with a glowing halo symbolizes its strong influence on the compound’s properties (basicity and lipophilicity). Building silhouettes represent places from all over Ukraine that have some special significance to the authors. Labels on the buildings indicate the key methods used for the compound physicochemical characterization. More information can be found in the Research Article by O. O. Grygorenko and co-workers (DOI: 10.1002/ejoc.202500728). Cover design by O. S. Liashuk.

A series of novel substituted biimidazo[1,5-a]pyridine derivatives are synthesized via a robust three-step, bidirectional approach. The strategy involves an initial Negishi homocoupling of bromopicolinonitrile, followed by the formation of diketones with aryl Grignard reagents, and concludes with a double cyclization using substituted arylamines to afford a library of biimidazo[1,5-a]pyridines. Selected dimers are structurally characterized by single-crystal X-ray diffraction. In addition, the impact of substitution patterns and connectivity within the biimidazo[1,5-a]pyridine framework on their photoluminescent properties is systematically investigated. The key substitution position on imidazo[1,5-a]pyridine core for tuning optical properties is identified. Furthermore, density functional theory (DFT) calculations are conducted to complement the experimental findings, offering a deeper understanding of the electronic structure, planarity, highest occupied molecular orbital and lowest unoccupied molecular orbital properties that influence their performance as organic light-emitting materials for optoelectronic applications.

A stereoselective synthesis of protected macrocyclic lactone core structure of 13E-disciformycin B was accomplished in a convergent fashion employing commercially available (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, tiglic aldehyde and (R)-Roche ester. Key transformations include an Aldol reaction, CBS reduction, Takai olefination, Julia olefination, Nozaki–Hiyama–Kishi (NHK) reaction, and Yamaguchi esterification reaction.

As a part of the ongoing COVID Moonshot project, an expedient approach to 1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylates is described. The method is based on a one-pot tandem Michael amination–lactamization sequence starting from 2-(3-alkoxymethoxy-3-oxoprop-1-en-2-yl)benzoic acids and primary amines. The scope of the N-nucleophiles included various aliphatic, aromatic, and heteroaromatic primary amines. The reaction tolerated and was compatible with ether, ester, amide, alcohol, carbamate, free alcohol, azole, or azine moieties. The developed protocol allowed for the preparation of target tetrahydroisoquinoline derivatives in 40%–75% yield on up to 109 g scale (later extended up to 0.86 kg). A mechanistic scheme involving a ring-chain tautomerism for the electrophilic component of the reaction is proposed. The method was used in the synthesis of DNDI-6510, a SARS-CoV-2 main protease inhibitor that showed promising results obtained in preclinical studies.

A highly efficient, metal-free, atom-economical green protocol for the synthesis of N,S-polyheterocycles via dearomative [3 + 2] cycloaddition of N-phenacylbenzothiazolium salts with alkylidene acenaphthylenones and barbiturate-derived alkenes. This reaction tolerates diverse substituents on the acenaphthylenone and barbiturate partners, underscoring its broad scope and providing an efficient method to construct desired cycloadducts in good to excellent yields with high diastereoselectivity. This strategy provides the formation of two CC bonds with multiple contiguous stereocenters, including one spiro-center, in a one-pot reaction. Significantly, no hydro-quenching, solvent separations, or chromatographic/recrystallization purifications are required. Overall, this efficient, selective, and eco-friendly strategy offers rapid access to N,S-frameworks relevant to medicinal chemistry and materials science.