Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3650 - 3665

Опубликована: Фев. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Язык: Английский

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Six‐Membered Aromatic Nitrogen Heterocyclic Anti‐Tumor Agents: Synthesis and Applications

The Chemical Record, Год журнала: 2023, Номер 23(12)

Опубликована: Ноя. 27, 2023

Cancer stands as a serious malady, posing substantial risks to human well-being and survival. This underscores the paramount necessity explore investigate novel antitumor medications. Nitrogen-containing compounds, especially those derived from natural sources, form highly significant category of agents. Among these, agents with six-membered aromatic nitrogen heterocycles have consistently attracted attention chemists pharmacologists. Accordingly, we present comprehensive summary synthetic strategies clinical implications these compounds in this review. entails an in-depth analysis synthesis pathways for pyridine, quinoline, pyrimidine, quinazoline. Additionally, historical progression, targets, mechanisms action, effectiveness small molecule inhibitors possessing structural features.

Язык: Английский

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Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Green Synthesis and Catalysis, Год журнала: 2021, Номер 2(2), С. 237 - 240

Опубликована: Март 28, 2021

The iron-catalyzed [4 ​+ ​2] annulation of α,β-unsaturated ketoxime acetates with enaminones has been developed, providing efficient access to highly substituted pyridines in moderate good yields. Notable features the present strategy include low-cost catalytic system, simple and mild reaction condition wide substrate scope. Mechanistic studies reveal that FeCl2 may directly serve as a Lewis acid activate for nucleophilic addition.

Язык: Английский

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Synthesis of Stable N–H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-c]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated O-Acyl Ketoximes with Isoquinolinium N-Ylides

Organic Letters, Год журнала: 2022, Номер 24(21), С. 3828 - 3833

Опубликована: Май 23, 2022

A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis stable N-H imines a benzo[7,8]indolizine core. When β-(2-bromoaryl)-α,β-unsaturated are used as starting materials, cascade cyclization occurs to afford benzo[7,8]indolizino[1,2-c]quinolines.

Язык: Английский

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Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review

RSC Advances, Год журнала: 2025, Номер 15(13), С. 9676 - 9755

Опубликована: Янв. 1, 2025

The tremendous potential of transition metal-free multi-component reactions (MCR) in the synthesis N-heterocyclic frameworks is examined this review, offering a complete overview subject matter. discussion on mechanistic rationale reaction routes and intermediates provides profound insights into underlying changes, encouraging deeper investigation various molecular frameworks. This review serves as doorway to study practicality exploiting these for efficient uncomplicated specific nitrogen heterocycles. Specifically, we reveal catalysts field. Because their extensive scope diversity, enable heterocycles that contain nitrogen, which include 5-membered (carbazole, pyrimidines, pyrroles) 6-membered rings (piperidine, pyridine, quinoline, diazinane, pyrazine, quinoxaline, 1,2,3-triazine). In addition, compatibility with functional groups substrates not only increases synthetic value compounds but also broadens relevance domains medical chemistry, materials science, other relevant areas study. To motivate future development field, successful examples described highlight powerful instruments quick general, thorough insightful examination catalysts, highlighting contemporary organic revolutionize field heterocycle synthesis.

Язык: Английский

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Recent advances and future challenges in the synthesis of 2,4,6-triarylpyridines

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(38), С. 8184 - 8204

Опубликована: Янв. 1, 2021

The present review is focused on recent advances (2015–present) in the synthesis of 2,4,6-triarylpyridines (also known as Kröhnke pyridines).

Язык: Английский

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Recent Advances in Synthesis of Multiply Arylated/Alkylated Pyridines

The Chemical Record, Год журнала: 2022, Номер 22(9)

Опубликована: Июнь 14, 2022

Abstract Multiply aryl/alkyl‐substituted pyridines are some of the untapped synthetic targets because challenge in regioselectively introducing less polar aryl/alkyl groups at desired positions pyridine framework. Interestingly, importance this family compounds has increased annually, particularly biological and materials engineering applications. The syntheses such have been extensively reported, but there is a lack comprehensive review articles. Hence, discusses recent advances by grouping reaction patterns that generally deliver tri‐, tetra‐, penta‐aryl/alkyl pyridines.

Язык: Английский

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Synthesis and biological activities of bicyclic pyridines integrated steroid hybrid

Steroids, Год журнала: 2023, Номер 199, С. 109287 - 109287

Опубликована: Июль 29, 2023

Язык: Английский

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Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and o‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(19), С. 4632 - 4638

Опубликована: Авг. 24, 2021

Abstract The iodine‐promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene‐substituted bis‐pyrazolo[3,4‐ b :4′,3′‐ e ]pyridines (BPPs), diuracilpyridines o ‐amino diheteroaryl ketones. procedure proceeded with easily available methyl azaarenes, 5‐aminouracils substituted 5‐aminopyrazoles. This protocol is a simple metal‐free approach which exhibits high functional group compatibility broad substrates scope. Moreover, this transformation can be applied preparation dipyrazolo/diuracil‐fused pyridines on gram scale. magnified image

Язык: Английский

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Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Beilstein Journal of Organic Chemistry, Год журнала: 2023, Номер 19, С. 820 - 863

Опубликована: Июнь 12, 2023

Pyridine is a crucial heterocyclic scaffold that widely found in organic chemistry, medicines, natural products, and functional materials. In spite of the discovery several methods for synthesis functionalized pyridines or their integration into an molecule, new methodologies direct functionalization pyridine scaffolds have been developed during past two decades. addition, transition-metal-catalyzed C–H rare earth metal-catalyzed reactions flourished over decades development molecules concern. this review, we discuss recent achievements transition-metal bond look mechanisms involved.

Язык: Английский

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