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

Panda, Jasmine; Raiguru, Bishnu Prasad; Mishra, Mitali; Mohapatra, Seetaram; Nayak, Smita

doi:10.1002/slct.202103987

Cited by 29 publications

(29 citation statements)

References 349 publications

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“…[ 60 ]. There are several methods for preparing imidazo[1,2-a]pyridine derivatives [ 61 ]; however, the Groebke–Blackburn–Bienaymé reaction (GBB) [ 62 ] is the most commonly used. In this three-component reaction, imidazo[1,2-a]pyridine derivatives 149 are prepared by a sequential combination of an aldehyde 150 with the 2- aminopyridines 151 and isocyanide 152 .…”

Section: Synthesis Of Heterocycles Using 13-diaza-13-butadienesmentioning

confidence: 99%

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

et al. 2022

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Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.

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Section: Synthesis Of Heterocycles Using 13-diaza-13-butadienesmentioning

confidence: 99%

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

et al. 2022

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“…In addition, imidazo[1,2‐ a ]pyridines with a 2‐hydroxyphenyl substituent at the 2‐position are essential in the optoelectronics field owing to the excited‐state intramolecular proton transfer (ESIPT) [11–13] . Due to multidisciplinary applications, several methods have been developed for its preparation; however, the three‐component one‐pot synthesis is a straightforward and efficient protocol [8–9,14–17] . In 2010, Gevorgyan et al.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

et al. 2023

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Development of catalysts using natural feedstock is the need of the current era, and accordingly, we have developed a new ligand N-(2-hydroxynapthylidene)-L-leucienyl-4,6-O-ethylideneβ-D-glucopyranosylamine using natural occurring D-glucose and L-amino acid. It interacts with several bio-relevant metal ions like iron, copper, zinc, etc., but its association with cupric ions is immune to pH (4.2-9.1) change. In-situ copper-catalyzed reactions have been proven to be pivotal in many important organic syntheses, including imidazo[1,2-a]pyridines, which is one of the important precursors of many drug molecules. Catalytic synthesis of imidazo[1,2-a]pyridines requires high catalyst loading, hazardous solvent, high temperature, and long reaction time, which are major drawbacks towards green synthetic methodology. Interestingly, our glycoconjugate-derived cupric complex catalyzes the reactions among aldehydes, 2-aminopyridines, and terminal alkynes under the solvent-free condition to afford one-pot synthesis of imidazo[1,2-a]pyridines and 23 derivatives have been reported in good to excellent yields (53-93 %) using lower reaction time, temperature, and catalyst loading compared to other reports on similar reactions. Hence, our approach enhances the green methodology towards the catalytic synthesis of imidazo[1,2-a]pyridine derivatives.

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“…Schiff base compounds are azomethinecontaining compounds formed through a condensation reaction between primary amine and carbonyl compounds, and they were first reported by Hugo Schiff in 1864 [14][15][16]. Schiff base compounds are a significant and well-studied class due to their wide variety of biological uses, simplicity of manufacturing, chelating properties, and stability [17][18][19]. In addition to their unique properties and practical uses, Schiff bases are also particularly fascinating compounds that shield metal ions from the chemical environment by creating kinetically inert complexes.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Lanthanide Metal Complexes with Schiff Base Ligand Produced from Reaction of 4,4-Methylene Diantipyrine with Ethylenediamine

Wang

Shaalan²

2022

Indones. J. Chem.

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An environmentally friendly method for the synthesis of Schiff bases was described by combining 4,4-methylenediantipyrine with ethylenediamine. The complex was prepared in a classical way, the usual condensation reaction method. A series of metal complexes were prepared from reactions of lanthanide nitrate salts [Nd+3, La+3, Er+3, Gd+3, and Dy+3] with a Schiff base ligand. The structures of the complexes were confirmed by analytical studies, spectral measurements, and thermal studies, and the prepared ligand was characterized using microanalysis technique, UV-Visible, infrared, nuclear magnetic resonance 1H-NMR and 13C-NMR, mass spectrometry, and thermogravimetric analysis (TGA), and the addition of conductivity measurement and magnetic moment of complexes. The results showed that these complexes have a consistency of 10 in which the elements are bonded with the ligand through the two nitrogen atoms at C=N and that the bonding ratio between the metal:ligand is in 1:2 ratio. By using agar disc-spreading, we tested several in vitro compounds for their antibacterial activity against four pathogenic bacteria, including Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae. The majority of the complexes demonstrated antibacterial activity.

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

Cited by 29 publications

References 349 publications

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Synthesis of Catalyst Using Bio‐benign Precursors and Its Application in One‐Pot Catalytic Synthesis of Imidazo[1,2‐a]pyridines

Synthesis, Characterization, and Antibacterial Activity of Lanthanide Metal Complexes with Schiff Base Ligand Produced from Reaction of 4,4-Methylene Diantipyrine with Ethylenediamine

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