Recent advances in multi-component reactions and their mechanistic insights: a triennium review

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(15), P. 4237 - 4287

Published: Jan. 1, 2021

This review summarizes the recent developments in MCRs, incorporating different strategies along with their mechanistic aspects.

Language: Английский

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Green and efficient one-pot three-component synthesis of novel drug-like furo[2,3-d]pyrimidines as potential active site inhibitors and putative allosteric hotspots modulators of both SARS-CoV-2 MPro and PLPro

Bioorganic Chemistry, Journal Year: 2023, Volume and Issue: 135, P. 106390 - 106390

Published: Jan. 28, 2023

Language: Английский

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4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(12), P. 3101 - 3126

Published: Oct. 22, 2021

Abstract One‐pot multi‐component reactions especially under transition‐metal‐free catalysis served as an efficient, and environmentally friendly method for the construction of value‐added compounds. Their importance in organic synthesis has drastically increased due to their operational simplicity, cost‐effectiveness, step‐ pot‐economic nature. On other hand, molecular hybridization concept recently emerged a key fascinating area medicinal chemistry design new drugs. Owing widespread occurrence natural products, pharmaceutical agents, incorporation another heterocycle either substituents or fused material into 4‐hydroxycoumarin moiety offers opportunities broad application targeted coumarin‐heterocycles many branches chemistry. Considering both topics, here we have reviewed developments achieved diverse medicinally privileged oxygen, nitrogen‐containing heterocycles well spiro‐heterocycles linked with coumarin by using readily accessible starting via one‐pot reaction conditions.

Language: Английский

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Elevating pyrrole derivative synthesis: a three-component revolution

Molecular Diversity, Journal Year: 2024, Volume and Issue: unknown

Published: May 21, 2024

Language: Английский

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An environmentally benign multi-component reaction: Highly regioselective synthesis of functionalized 2-(diarylphosphoryl)-1,2-dihydro-pyridine derivatives

Green Synthesis and Catalysis, Journal Year: 2021, Volume and Issue: 3(1), P. 59 - 68

Published: Oct. 25, 2021

A novel protocol was developed for the construction of highly functionalized 2-(diarylphosphoryl)-1,2-dihydropyridine derivatives (DAPDHPs) from 3-formylchromones (1), heterocyclic ketene aminals (HKAs, 2), and phosphine oxides (R2P(O)H, 3) via a novel, one-pot cascade reaction. Optimization reaction conditions determined that refluxing mixture 3-formylchromones, HKAs, various R2P(O)H in propylene carbonate (PC) presence triethylamine as base facilitated highest yields DAPDHP products. This reaction, which involved cleavage one C–O bond 3-formylchromone substrates formation three new bonds (one C–C, C–N, C–P bond), enabled synthesis small library The dearomatized products were formed by regioselective nucleophilic addition reagents to intermediate pyridinium salts 8. approach has several advantages such use an environmentally-friendly solvent, simple practical operation (with filtration washing without column chromatography separation), good yields, product with potential biological activity.

Language: Английский

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(9)

Published: July 29, 2023

Abstract Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, use transition metal catalysts or additives MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest metal‐free N ‐heterocyclic compounds. This review provides comprehensive concise overview advancements valuable ‐heterocycles over past five years. The is systematically organized, categorizing discussed based on size heterocyclic ring number nitrogen atoms. Only that result formation rings containing at least one atom are included, while derivatization using falls outside scope this review. By highlighting developments field, aims showcase potential significance sustainable strategies accessing elimination metals not only simplifies reaction conditions but also contributes greener more environmentally friendly approaches. serves resource researchers interested design application

Language: Английский

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Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

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

Published: March 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Language: 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, Journal Year: 2025, Volume and Issue: 15(13), P. 9676 - 9755

Published: Jan. 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.

Language: Английский

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Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(9), P. 1217 - 1220

Published: Jan. 1, 2023

A novel protocol for the synthesis of highly functionalized benzo[b][1,5]diazocin-6(5H)-one derivatives (BDCOs, 4 and 5) from 2-aryl-1H-indoles 1,1-enediamines was developed via a complex cascade reactions including regioselective free radical oxidation, 1,2-addition imine, imine-enamine tautomerization, intramolecular cyclization, ring expansion. The reaction enabled by refluxing mixture two substrates in presence di-tert-butyl peroxide (DTBP) as an oxidant anhydrous CuI catalyst toluene under argon protection. Consequently, series BDCOs (4 were synthesized with high regioselectivity good yield. This can be used one-pot oxidative annulation rather than multi-step reaction, which is suitable both combinatorial parallel syntheses BDCOs.

Language: Английский

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Synthesis of Pyrrole via Formal Cycloaddition of Allyl Ketone and Amine under Metal-Free Conditions

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(18), P. 12482 - 12490

Published: Sept. 2, 2022

A new metal-free synthesis of pyrrole from allyl ketone and amine has been established. The reaction proceeds via an thiolative activation the C–C double bond with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by a nucleophilic ring-opening addition primary to generated episulfonium intermediate, then internal condensation aromatization. This mild procedure provides novel strategy construction substituted pyrroles through formal [4 + 1] cycloaddition reaction.

Language: Английский

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