Recent Advancements in Pyrrole Synthesis

Synthesis, Journal Year: 2021, Volume and Issue: 53(09), P. 1531 - 1555

Published: March 17, 2021

This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle can be found in numerous compounds biological material significance. Given its vast importance, pyrrole continues to attractive target for development new synthetic reactions. The contents this are organized by starting materials, which broadly classified into four different types: substrates bearing π-systems, carbonyl other polar groups, heterocyclic motifs. Brief discussions plausible reaction mechanisms most transformations also presented.

Language: Английский

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Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(3)

Published: Jan. 21, 2022

Abstract This review focuses on providing comprehensive highlights of the recent synthetic pathways imidazo[1,2‐ a ]pyridines, assisted through transition metal‐catalyzed reactions, multi‐component cyclization, condensation, microwave‐assisted heteroannular and photocatalytic reactions. Among heterocyclic groups, ]pyridines are considered as privileged structures because their occurrence in many natural products. In this review, we have summarized advances synthesis from 2016 to 2021 various substrates. will provide new initiatives chemists towards all frequent challenges associated with reported methods.

Language: Английский

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Arylation of α‐Imino Ketones and their Cyclization with Allenoates: Direct Access to Sterically Hindered Pyrroles

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

Published: Jan. 28, 2025

Abstract Herein, we report a calcium‐catalyzed, one‐pot, four‐component reaction to synthesize diversely substituted pyrroles. This atom‐economy involves sequence of reactions that proceed via in situ formation α ‐ imino ketones, Friedel‐Crafts arylation, aza‐cyclization, and aromatization the single pot. The showed broad substrate scope with good yields. We demonstrated gram‐scale synthesis post‐synthetic modifications.

Language: Английский

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Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(22), P. 9908 - 9914

Published: May 12, 2020

Herein, we describe an efficient method to prepare polysubstituted pyrroles via a copper hydride (CuH)-catalyzed enyne-nitrile coupling reaction. This protocol accommodates both aromatic and aliphatic substituents broad range of functional groups, providing variety N-H in good yields with high regioselectivity. We propose that the Cu-based catalyst promotes initial reductive subsequent cyclization steps. Density theory (DFT) calculations were performed elucidate reaction mechanism.

Language: Английский

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Recent advances in the coordination chemistry of benzotriazole-based ligands

Coordination Chemistry Reviews, Journal Year: 2019, Volume and Issue: 395, P. 193 - 229

Published: June 15, 2019

Language: Английский

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Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles

Nanomaterials, Journal Year: 2020, Volume and Issue: 10(12), P. 2405 - 2405

Published: Dec. 1, 2020

We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards selective reaction between o-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several nanoparticle platforms, Au/TiO2 provides a series 2-aryl 2-alkyl substituted benzimidazoles at ambient conditions, in absence additives high yields, using mixture CHCl3:MeOH ratio 3:1 as solvent. AuNPs catalysts used herein, containing small-size is found to be most active present methodology. The can recovered reused least five times without significant loss its efficacy. synthetic protocol applies broad substrate scope represents an efficient method for formation C–N bond under mild conditions. Notably, this methodology regio-isomer anthelmintic drug, Thiabendazole, lab-scale showing applicability synthesis such N-heterocyclic molecules industrial levels.

Language: Английский

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Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Catalysts, Journal Year: 2022, Volume and Issue: 12(6), P. 660 - 660

Published: June 15, 2022

The multicomponent reaction of aldehydes, amines, and alkynes, known as A3 coupling, yields propargylamines, a valuable organic scaffold, has received significant interest attention in the last years. In order to fully realise potential metal-based catalytic protocols that facilitate this transformation, we summarise substrates, situ well-characterised synthetic methods provide scaffold attempt monumental classification considering several variables (Metal, Coordinating atom(s), Ligand type name, in-situ or well-characterised, co-catalyst, catalyst ligand Loading (mol%), solvent, volume, atmosphere, temperature, microwave, time, yield, selectivity (e.e. d.r.), substrate functionality, loading (amines, alkynes), use molecular sieves). This pioneering work creates database contains 2376 entries allows us produce graphs better visualise their impact on reaction.

Language: Английский

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An overview on the copper‐promoted synthesis of five‐membered heterocyclic systems

Applied Organometallic Chemistry, Journal Year: 2020, Volume and Issue: 34(5)

Published: March 3, 2020

The development of novel approaches for the preparation small‐sized heterocyclic products has remained an extremely attractive but challenging proposition. Copper been known as one most applicable and significant transition metals utilized in synthesis organic products. A couple factors such high earth abundance versatile catalysis resulted growth copper‐promoted five‐membered Utilizations making coins electrical equipment express importance copper, well. Here, a comprehensive overview copper‐catalyzed is presented, focusing on developments over past 4 years.

Language: Английский

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Enal-Azomethine Ylides: Application to the Synthesis of Functionalized Pyrroles

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5734 - 5738

Published: Jan. 1, 2024

Rhodium-catalyzed [3 + 2] annulation of diazoenals and

Language: Английский

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Efficient Synthesis of Polysubstituted Pyrroles Based on [3+2] Cycloaddition Strategy Utilizing [1,2]‐Phospha‐Brook Rearrangement under Brønsted Base Catalysis

Chemistry - A European Journal, Journal Year: 2018, Volume and Issue: 24(57), P. 15246 - 15253

Published: Aug. 16, 2018

Abstract An efficient method for the synthesis of polysubstituted pyrroles was established based on [3+2] cycloaddition strategy utilizing [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis. The less‐explored approach cycloaddition, that is, reaction a C3 subunit with imines, successfully achieved by making use newly designed subunits containing requisite umpolung . two‐step formal involves catalytic generation an α‐oxygenated propargyl anion through followed γ‐addition to imine catalysis and subsequent intramolecular cyclization mediated Au catalyst or halogenation reagent afford having variety substituents in positional selective manner. thus synthesized were amenable further transformations, such as palladium‐catalyzed cross‐coupling reactions. operationally very simple readily available substrates provides new access diverse array well‐organized pyrroles.

Language: Английский

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