Regiodivergent Arylation of Pyridines via Zincke Intermediates DOI Creative Commons
Haiwen Wang, Michael F. Greaney

Angewandte Chemie, Год журнала: 2023, Номер 136(8)

Опубликована: Ноя. 21, 2023

Abstract An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed at putative C4 position. Recyclization then provides pyridine products. Alternatively, metal‐free diaryliodonium salt selective meta ‐position, affording regiodivergent approach to biaryls from common

Язык: Английский

C–H Functionalization of Pyridines via Oxazino Pyridine Intermediates: Switching to para-Selectivity under Acidic Conditions DOI
Hui Cao,

Debkanta Bhattacharya,

Qiang Cheng

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(28), С. 15581 - 15588

Опубликована: Июль 10, 2023

para-Selective C-H functionalization of pyridines holds a significant value but remains underdeveloped. Site-switchable under easily tunable conditions expedites drug development. We recently reported redox-neutral dearomatization-rearomatization strategy for meta-C-H via oxazino pyridine intermediates. Here, we demonstrate that these intermediates undergo highly para-selective simply by switching to acidic conditions. A broad scope para-alkylated and arylated is prepared through radical as well ionic pathways. These mild catalyst-free methods are applied the late-stage para-functionalization drugs using limiting reagents. Consecutive meta,para-difunctionalization also achieved with complete regiocontrol relying on pH-dependent reactivity pyridines.

Язык: Английский

Процитировано

32

Enantioselective C3‐Allylation of Pyridines via Tandem Borane and Palladium Catalysis DOI

Jun‐Jie Tian,

Rui‐Rui Li,

Gui‐Xiu Tian

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(34)

Опубликована: Июль 3, 2023

Abstract Herein, we report a one‐pot method for enantioselective C−H allylation of pyridines at C3 via tandem borane and palladium catalysis. This involves borane‐catalyzed pyridine hydroboration to generate dihydropyridines, then palladium‐catalyzed the dihydropyridines with allylic esters, finally air oxidation allylated afford products. enables introduction an group excellent regio‐ enantioselectivities.

Язык: Английский

Процитировано

28

Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents DOI Creative Commons
Nagwa M. Abdelazeem, Wael M. Aboulthana,

Ashraf S. Hassan

и другие.

Saudi Pharmaceutical Journal, Год журнала: 2024, Номер 32(5), С. 102025 - 102025

Опубликована: Март 12, 2024

Based on previous developments of our research programs in trying to find new compounds with multiple biological targets such as antioxidant, anti-diabetic, anti-Alzheimer's, and anti-arthritic agents. In the context, a novel series sulfonamide derivatives based pyrazole or pyridine moieties 3a, b, 7–9, 11–13, 15a, 16 were synthesized from amine sulfonyl chloride derivatives. The structures elucidated via spectroscopy (1H 13C NMR). biologically assessed vitro for their anti-diabetic (α-amylase α-glucosidase inhibition) anti-Alzheimer's (acetylcholinesterase activities. results revealed that compound 15a is powerful enzyme inhibitor α-amylase α-glucosidase. Also, 15b demonstrated activity against acetylcholinesterase enzyme. structure–activity relationship study was accomplished. Furthermore, complementary silico molecular properties, drug-likeness, ADMET prediction, surface properties two more fulfilled computed. These studies recommend candidates modifications before vivo assays.

Язык: Английский

Процитировано

15

Introduction of the difluoromethyl group at the meta- or para-position of pyridines through regioselectivity switch DOI Creative Commons
Pengwei Xu, Zhe Wang, Shu‐Min Guo

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Май 15, 2024

Abstract Difluoromethyl pyridines have gained significant attention in medicinal and agricultural chemistry. The direct C−H-difluoromethylation of represents a highly efficient economic way to access these azines. However, the meta-difluoromethylation has remained elusive methods for site-switchable regioselective meta- para-difluoromethylation are unknown. Here, we demonstrate meta-C−H-difluoromethylation through radical process by using oxazino pyridine intermediates, which easily accessed from pyridines. selectivity can be readily switched para situ transformation pyridinium salts upon acid treatment. preparation various para-difluoromethylated this approach is presented. mild conditions used also allow late-stage or containing drugs. Sequential double functionalization presented, further underlines value work.

Язык: Английский

Процитировано

13

meta-Nitration of Pyridines and Quinolines through Oxazino Azines DOI
Kuruva Balanna, Armido Studer

Journal of the American Chemical Society, Год журнала: 2025, Номер 147(9), С. 7485 - 7495

Опубликована: Фев. 24, 2025

meta-Nitration of azines (pyridines and quinolines) serves as a powerful method for the prompt construction derivatization several pharmaceuticals, agrochemicals, materials. However, due to inherent electronic properties pyridines, achieving direct selective meta-C-H nitration under mild conditions has been long-standing challenge in synthetic chemistry. Currently, there is no adequate strategy late-stage pyridine-containing drugs drug precursors. To address this void, we introduce practical protocol highly regioselective meta-nitration pyridines using dearomatization-rearomatization strategy. The introduced provides diversification platform at meta-position via radical pathway. This mild, open-air, one-pot, scalable, catalyst-free process employed pyridine containing drugs, precursors, ligands limiting reagents. Consecutive C3 C5 difunctionalization also achieved with complete regiocontrol relying on sequential addition, which further highlights potential presented work. Additionally, obtained products could be transformed into meta-amino azine other valuable building blocks. Incorporating N-heterocyclic amine structures through amidation ibuprofen significantly improved drug's clinical success, highlighting importance

Язык: Английский

Процитировано

1

Indole-Pyridine Carbonitriles as Potential Anti-diabetic Agents: A Computational Study Using 3D-QSAR, Molecular Docking, ADME-Tox and Molecular Dynamics Simulations DOI
L. Naanaai, Mohamed Ouabane, Abdellah El Aissouq

и другие.

Chemistry Africa, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Язык: Английский

Процитировано

1

C3 Selective Hydroxylation of Pyridines via Photochemical Valence Isomerization of Pyridine N-Oxides DOI

Chen-Yan Cai,

Si-Jie Chen,

Rohan R. Merchant

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(35), С. 24257 - 24264

Опубликована: Авг. 22, 2024

The C–H hydroxylation of the pyridine C3 position is a highly desirable transformation but remains great challenge due to inherent electronic properties this heterocycle core which bring difficulties in chemical reactivity and regioselectivity. Herein we present an efficient method for formal selective pyridines via photochemical valence isomerization N-oxides. This metal-free features operational simplicity compatibility with diverse array functional groups, resulting hydroxylated products are amenable further elaboration synthetically useful building blocks. synthetic utility strategy demonstrated effective late-stage functionalization pyridine-containing medicinally relevant molecules versatile derivatizations 3-pyridinols.

Язык: Английский

Процитировано

8

Formal meta-C–H-Fluorination of Pyridines and Isoquinolines through Dearomatized Oxazinopyridine Intermediates DOI
Malte Haring, Kuruva Balanna, Qiang Cheng

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(45), С. 30758 - 30763

Опубликована: Ноя. 1, 2024

Organofluorine compounds, including fluorinated pyridines and isoquinolines, play a crucial role in pharmaceuticals, agrochemicals, materials science. However, step-economic selective C-H-functionalization to access these azaarenes is still underexplored, with

Язык: Английский

Процитировано

7

Regiodivergent Arylation of Pyridines via Zincke Intermediates DOI Creative Commons
Haiwen Wang, Michael F. Greaney

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(8)

Опубликована: Ноя. 21, 2023

Abstract An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed at putative C4 position. Recyclization then provides pyridine products. Alternatively, metal‐free diaryliodonium salt selective meta ‐position, affording regiodivergent approach to biaryls from common

Язык: Английский

Процитировано

15

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

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(26)

Опубликована: Апрель 18, 2024

C(sp

Язык: Английский

Процитировано

5