Synthesis of Polysubstituted Imidazo[1,2-<i>a</i>]pyridines via Microwave-Assisted One-Pot Cyclization/Suzuki Coupling/Palladium-Catalyzed Heteroarylation

Koubachi, Jamal; Kazzouli, Saı̈d El; Berteina‐Raboin, Sabine; Mouaddib, Abderrahim; Guillaumet, Gérald

doi:10.1021/jo0712603

Cited by 92 publications

(33 citation statements)

References 32 publications

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“…In the same year, our group developed two efficient methods for the synthesis of 2,3,6‐trisubstituted imidazo[1,2‐ a ]pyridine derivatives 96. The first method furnished the desired compounds 164 by a microwave‐assisted one‐pot, two‐step Suzuki/heteroarylation sequence from 6‐bromoimidazo[1,2‐ a ]pyridines 163 .…”

Section: Regiocontrolled Double Functionalization By Means Of Metamentioning

confidence: 99%

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

et al. 2014

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Section: Regiocontrolled Double Functionalization By Means Of Metamentioning

confidence: 99%

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

et al. 2014

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“…Their biological activities have been profusely investigated and as a consequence reports abound on the subject [1-3]. Theoretical calculations have also been performed on the system, aimed to explain its reactivity [4,5].…”

Section: Introductionmentioning

confidence: 99%

Intramolecular H-bonding interaction in angular 3-π-EWG substituted imidazo[1,2-a]pyridines contributes to conformational preference

Velázquez-Ponce

Salgado-Zamora

Jiménez‐Vázquez

et al. 2013

Chemistry Central Journal

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BackgroundThe proton at position 5 of imidazo[1,2-a]pyridines substituted with an angular electron withdrawing group (EWG) at position 3, shows an unusual downfield chemical shift, which is usually explained in terms of a peri effect. However usage of this term is sometimes confusing. In this investigation, it is proposed that the aforementioned shift is in fact a combination of several factors: Anisotropy, long-distance mesomerism and an attractive intramolecular interaction of the electrostatic hydrogen bond type.ResultsTheoretical calculations were performed aimed to obtain evidence of the existence of an intramolecular non-bonding interaction between H-5 and the oxygen atom of the EWG. Results derived from conformational and vibrational analysis at the DFT B3LYP/6-311++G(d,p) level of theory, the determination of Bond Critical Points derived from AIM theory, and the measurement of some geometrical parameters, support the hypothesis that the higher stability of the prevailing conformation in these molecules (that in which the oxygen of the EWG is oriented towards H-5) has its origin in an intramolecular interaction.ConclusionComputational calculations predicted correctly the conformational preferences in angular 3-π-EWG-substituted imidazo[1,2-a]pyridines. The existence of an electrostatic hydrogen bond between H-5 and the oxygen atom of the π-EWG was supported by several parameters, including X-ray crystallography. The existence of such structural array evidently impacts the H-5 chemical shift.

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“…Indeed they are known for their anxiolytic [1], cardiovascular [2], analgesic [3,4], antihypertensive [4] and neuroleptic [5,6] among other activities [7-9]. However, imidazo[1,2-a]pyridines and pyrimidines are also attractive due to their physicochemical properties exhibited, namely the fluorescent activity.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives

Velázquez-Olvera

Salgado-Zamora

Velázquez-Ponce

et al. 2012

Chemistry Central Journal

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BackgroundImidazo[1,2-a]pyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. The effect on the luminescent property by substituents in the heterocycle and phenyl rings, have been studied as well. In this investigation, series of 3-hydroxymethyl imidazo[1,2-a]pyridines and pyrimidines were synthesized and evaluated in relation to fluorescence emission, based upon the hypothesis that the hydroxymethyl group may act as an enhancer of fluorescence intensity.ResultsCompounds of both series emitted light in organic solvents dilutions as well as in acidic and alkaline media. Quantitative fluorescence spectroscopy determined that both fused heterocycles fluoresced more intensely than the parent unsubstituted imidazo[1,2-a]azine fluorophore. In particular, 3-hydroxymethyl imidazo[1,2-a]pyridines fluoresced more intensely than 3-hydroxymethyl imidazo[1,2-a]pyrimidines, the latter emitting blue light at longer wavelengths, whereas the former emitted purple light.ConclusionIt was concluded that in most cases the hydroxymethyl moiety did act as an enhancer of the fluorescence intensity, however, a comparison made with the fluorescence emitted by 2-aryl imidazo[1,2-a]azines revealed that in some cases the hydroxymethyl substituent decreased the fluorescence intensity.

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Synthesis of Polysubstituted Imidazo[1,2-a]pyridines via Microwave-Assisted One-Pot Cyclization/Suzuki Coupling/Palladium-Catalyzed Heteroarylation

Cited by 92 publications

References 32 publications

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

Intramolecular H-bonding interaction in angular 3-π-EWG substituted imidazo[1,2-a]pyridines contributes to conformational preference

Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives

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