First total synthesis of caerulomycin K: a case study on selective, multiple C–H functionalizations of pyridines DOI Creative Commons
Alessandro Dimasi, Mattia Failla, Arianna Montoli

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(8), P. 5542 - 5546

Published: Jan. 1, 2024

A radical change: the first 3-steps total synthesis of caerulomycin K was achieved exploiting Minisci chemistry using cheap starting materials.

Language: Английский

Mechanosynthesis of polysubstituted pyridines via FeBr3-catalyzed cascade reaction of arylidene isoxazolones with β‑carbonyl esters DOI
Lei Wang, Mingjun Li, Qinghai Li

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155569 - 155569

Published: March 1, 2025

Language: Английский

Citations

0
Visible-light-induced meta-selective sulfonylation of pyridine via an EDA complex DOI

Yong-Qing Ye,

Zhipeng Ye,

Meng Guo

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Pyridine is a versatile structural unit found in broad spectrum of pharmaceuticals, agrochemicals, and materials. Achieving selective meta-functionalization under mild conditions remains challenging due to its inherent electronic properties. In this work, we accomplished photoinduced method for meta-selective sulfonylation pyridines, facilitated by an electron donor-acceptor (EDA) complex between iodide ions sulfonyl chlorides. The reaction proceeds via oxazino-pyridine intermediate, with chloride acting as the radical precursor. This protocol stands out mild, photocatalyst-free conditions, high C5-selectivity, good scalability, offering promising approach synthesis meta-sulfonylated pyridines.

Language: Английский

Citations

0
Fluorescent pyridine phosphonium salts via transmutation of metallabenzenes DOI Creative Commons
Yaowei Zhang,

Feifei Han,

Zhihong Yin

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 16, 2025

Metallabenzenes are recognized as a unique class of aromatic compounds, not only structural and theoretical interest but also platforms to design powerful transformations. Here, we report the successful transmutation metallabenzene for pyridine synthesis. This 'metal-to-nitrogen swapping' process utilizes readily available ruthenabenzene phosphonium salts commercially 2-aminopyridines under mild conditions. The isolation ruthena-azepines, containing planar seven-membered aza-metallacycle, along with DFT calculations, supports nitrogen insertion/metal deletion cascade driven by aromatization. Additionally, investigate tunable photophysical properties resulting salts.

Language: Английский

Citations

0
A difluoroboron compound with latent fingerprint detection and inkless writing based on aggregation-induced emission enhancement and mechanofluorochromic behavior DOI

Shufang Yang,

Jiazhuang Tian,

Bangcui Zhang

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 48(3), P. 1264 - 1271

Published: Dec. 8, 2023

A pyridine-based difluoroboron compound with the TPA group displayed excellent AIEE activity and MFC behavior, which was applied for latent fingerprint detection inkless writing.

Language: Английский

Citations

10
Advances in Pyridine C – H Functionalizations: Beyond C2 Selectivity DOI
Sachin Balaso Mohite, Yafia Kousin Mirza, Partha Sarathi Bera

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(2)

Published: Nov. 28, 2024

The pyridine core is a crucial component in numerous FDA-approved drugs and Environmental Protection Agency (EPA) regulated agrochemicals. It also plays significant role ligands for transition metals, alkaloids, catalysts, various organic materials with diverse properties, making it one of the most important structural frameworks. However, despite its significance, direct selective functionalization still relatively underdeveloped due to electron-deficient nature strong coordinating ability nitrogen. Among variety synthetic transformation, C-H bond straightforward atom economical approach it's advantageous late-stage containing drugs. In recent years, innovative strategies regioselective pyridines azines have emerged, offering benefits such as high regioselectivity, mild conditions, enabling transformations that were challenging traditional methods. This review emphasizes latest advancements meta para-C-H through approaches, including phosphonium salts, photocatalytic methods, temporary de-aromatization, Minisci-type reactions, metal-catalyzed activation techniques. We discuss advantages limitations these current methods aim inspire further progress this field.

Language: Английский

Citations

3
Multi-faceted spectroscopic, computational, and nonlinear optical characterization of 2-(pyrrolidin-1-yl)-3,5-dinitropyridine DOI

Takwa Slama,

Zouhour Mazouz,

Balkis Abdelaziz

et al.

Journal of Molecular Liquids, Journal Year: 2024, Volume and Issue: unknown, P. 126722 - 126722

Published: Dec. 1, 2024

Language: Английский

Citations

2
Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate DOI Creative Commons
Yiwei Gong, Jas S. Ward, Kari Rissanen

et al.

Molbank, Journal Year: 2023, Volume and Issue: 2023(3), P. M1710 - M1710

Published: Aug. 9, 2023

Site-selective functionalization of pyridines is a crucial tool for the synthesis diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient potent Lewis acids. report that tributylphosphine selectively adds to 4-position in tetramethyldiiminium ditrifluoromethanesulfonate, resulting formation title compound. This finding represents an advancement towards utilization units organic reagents or catalysts functionalization. also employ computational models determine fluoride hydride ion affinities, Fukui function f+(r), molecular electrostatic potential, pKa values, providing valuable insights future investigations this area.

Language: Английский

Citations

4
Meta‐Selective Copper‐Catalyzed C–H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates DOI Creative Commons
Shu‐Min Guo, Pengwei Xu, Armido Studer

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(26)

Published: April 18, 2024

Abstract C(sp 2 )−H functionalization offers an efficient strategy for the synthesis of various elaborated N ‐containing heteroarenes. Along these lines, oxazino pyridines that can be readily prepared from pyridines, have been introduced as powerful substrates in radical‐ and ionic‐mediated meta ‐C−H functionalization. However, regioselective arylation remains a great challenge. Herein, copper‐catalyzed ‐selective C−H isoquinolines through bench‐stable dearomatized intermediates is reported. Electrophilic aryl‐Cu(III) species, generated accessible aryl I(III) reagents, enable ‐arylation broad range isoquinolines. The method also allows alkenylation heteroarenes using corresponding alkenyl I(III)‐reagents. Late‐stage drug‐derived larger‐scale experiments demonstrate potential this synthetic methodology.

Language: Английский

Citations

1
Organocatalytic access to 3-pyridylphosphonates from vinyl phosphonates and aldehydes DOI

Ram Subhawan Verma,

Anil Kumar Khatana,

Deepika Verma

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(40), P. 5306 - 5309

Published: Jan. 1, 2024

The preparation of 3-phosphorylated pyridines has remained the most challenging compared to corresponding 2- or 4-functionalized pyridines.

Language: Английский

Citations

1
Iron-Catalyzed Functionalization of Heterocycles Through C─H Activation DOI
Chandini Pradhan, Benudhar Punji

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 32

Published: Jan. 1, 2024

Language: Английский

Citations

1