Synthesis and site selective C–H functionalization of imidazo-[1,2-a]pyridines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(36), P. 7267 - 7289

Published: Jan. 1, 2023

Herein we disclose the synthesis and an overview of all functionalization reactions at each carbon atom, viz , C2, C3, C5, C6, C7 C8 imidazo[1,2- a ]pyridine.

Language: Английский

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Functionalization of Indoles with 1,3,5-Triazinanes: Chemistry of Aminomethylation vs the Hofmann–Martius-Type Rearrangement

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

Published: Jan. 29, 2025

We have developed efficacious routes toward the selective synthesis of two classes compounds such as C-3 amino-methylated indoles and 4-indol-3-yl-methylanilines from same precursors, namely, 1,3,5-triazinanes. It is reported that controlled cleavage 1,3,5-triazinanes can be effected by heat for generation aryl imine motifs, we observed presence Lewis acid influences course these transformations different products. The reaction indol-3-yl-methylanilines proceeds via a nucleophilic attack indole to generated form an product which undergoes mediated Hofmann-Martius-type rearrangement. In absence acid, between 1,3,5-triazinane afforded indoles. Experimentally, could prove was intermediate formed during catalyzed process in intermolecular fashion. both found general, library molecules generated.

Language: Английский

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[2+2+1+1] Cycloaddition Reaction of 1,3,5‐Triazinanes with Methylene Compounds: Approach to Hexahydropyrimidines

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3909 - 3914

Published: Aug. 16, 2023

Abstract An acetic acid‐catalyzed [2+2+1+1] cycloaddition of 1,3,5‐triazinanes with methylene compounds was developed. This protocol provides an access to hexahydropyrimidines (HHPs) (25 examples) in 35–99% yields under mild conditions 2 hours. The potential application this method demonstrated by gram‐scale synthesis. Preliminary mechanistic investigation conducted elucidate the possible mechanism. work represents yet unknown example reaction between and active compounds.

Language: Английский

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Two-photon absorption in imidazo[1,2-a]pyridine derivatives: Study of nonlinear optical response and dipolar properties

Journal of Molecular Liquids, Journal Year: 2023, Volume and Issue: 373, P. 121250 - 121250

Published: Jan. 13, 2023

Language: Английский

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Reaction of imidazo[1,2-a]pyridines with coumarin-3-carboxylic acids: a domino Michael addition/decarboxylation/oxidation/annulation

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(40), P. 19455 - 19459

Published: Jan. 1, 2022

A palladium-catalyzed decarboxylative domino reaction of imidazo[1,2- a ]pyridines and coumarin-3-carboxylic acids has been developed, which provides access to dibenzoisochromenoimidazo[1,2- ]pyridin-6-ones possessing six fused rings.

Language: Английский

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Catalyst-free inverse-electron-demand aza-Diels–Alder reaction of 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes: access to polysubstituted tetrahydropyridines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5413 - 5418

Published: Jan. 1, 2023

An inverse-electron-demand aza-Diels–Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free additive-free conditions was developed.

Language: Английский

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Shifting Access from Pyrimidine‐Spirofused to Fused Benzoheterocycles by Modifying the Activated Group Position

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1096 - 1100

Published: Jan. 19, 2024

Abstract The synthesis of pyrimidine‐spirofused indolines from 1,3,5‐triazinanes with 2‐sulfonyliminoindolines has been achieved under catalyst‐ and additive‐free conditions, in which five atoms were introduced to the spiro‐annulation products via a (5+1) pathway. Subsequently, this strategy was extended 3‐aminoindoles 3‐aminobenzothiophenes, but different reaction pathway (3+3) observed. In these cases, three‐atoms incorporated into pyrimidine‐fused indoles/benzothiophenes. These two transformations demonstrate potential versatility construct nitrogen‐heterocycles.

Language: Английский

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Propriedades fotofísicas de derivados de imidazo[1,2->i<a>/i<]piridina

Published: July 13, 2023

Currently, there is great interest in organic molecules with π-conjugated systems due to significant advances molecular engineering, which have enabled the modulation of optical properties compounds for specific purposes.The nonlinear optics field has benefited from these advances, particularly context two-photon absorption (2PA) processes compounds.This important implications applications such as 2PA fluorescence microscopy and photodynamic therapy, among others.A materials class that attracted considerable attention derived imidazo[1,2-a]pyridine (IP), its similarity purine good emissive properties, making it highly interesting involving fluorescent markers various molecules, especially DNA RNA.However, knowledge photophysical IP still limited, only a few spectroscopic studies available on this molecule.In order expand potential derivatives, necessary conduct systematic address their linear characteristics.In dissertation, we present detailed study seven new derivatives dissolved dimethyl sulfoxide (DMSO).The studied here contain different peripheral groups, some are structures strong electron-donating or electron-withdrawing character, while others enhance effective conjugation.These groups can modify typical molecule act amplify modulate properties.The objective work understand influence relation 2PA.For purpose, techniques were employed elucidate fundamental aspects compounds.The Z-scan technique was used determine spectrally resolved cross-section all samples.In addition, quantum chemical calculations performed using density functional theory, including timedependent calculations, contribute interpretation experimental data.By employing techniques, observed increase conjugation, provided by naphthalene substituent, results an approximately 7-fold 2PA.This behavior also when character added core imidazo[1,2-a]pyridine.These suggest responses ( 2 ≈ 20 ) be achieved less conjugated structures, possess electronwithdrawing appropriately positioned.Thus, understanding obtained.It expected investigation materials, imidazo[1,2-a]pyridine, aiming applications.

Language: Английский

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Five-membered ring systems: with more than one N atom

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 281 - 332

Published: Jan. 1, 2023

Language: Английский

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