Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

Shahrisa, Aziz; Safa, Kazem D.; Esmati, Somayeh

doi:10.1016/j.saa.2013.09.056

Cited by 23 publications

(20 citation statements)

References 47 publications

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“…On 4H-pyran-4-one (4-pyrone) derivatives are widely distributed in a variety of bio-active compounds [22][23][24][25][26]. We have therefore designed a synthetic strategy for molecules bearing both xanthene and pyrone fragments.…”

Section: Resultsmentioning

confidence: 99%

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Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

et al. 2015

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An efficient green method for the syntheses of biologically active xanthene derivatives by use of zeolite-supported transition metal catalysts is described. A Fe-Cu/ZSM-5 heterogeneous catalyst has the highest activity in the one-pot syntheses with a wide range of aldehydes and cyclic 1,3-diketones, under ultrasonic irradiation in water at ambient temperatures. The three-component condensation in the presence of supported metal catalysts is operationally simple, requires no expensive or toxic reagents, and gives high yields in short reaction times.

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Section: Resultsmentioning

confidence: 99%

“…As shown in Scheme 2, 5-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde was obtained from commercially available Kojic acid [5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one] by benzylation of the phenolic OH [26], followed by oxidation of …”

Section: Resultsmentioning

confidence: 99%

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

et al. 2015

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“…In 2014, imidazo[1,2-a]pyridines 68 possessing a 5-benzyloxy-4H-pyran-4-one moiety were found to exhibit the highest fluorescence emissions in dichloromethane com- pared to other GBBR products [43]. The photophysical properties of these compounds showed a fluorescence quantum yields ( f = 0.209 and 0.203) and relatively Stokes shifts (≈ 120 nm) ( Fig.…”

Section: Applications Of Gbbr In Drug Discoverymentioning

confidence: 92%

“…For example, 3-aminoimidazo[1,2-a]pyridines possessing 4-pyrone 7 were synthesized using the 4-pyrone carbaldehydes 6 as the aldehyde component (Scheme 2; [43]). …”

Section: Variations Of the Aldehyde Componentmentioning

confidence: 99%

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

2015

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The Groebke-Blackburn-Bienaymé reaction (GBBR) is used for the one-pot synthesis of therapeutically relevant fused imidazoles bridgehead nitrogen heterocyclic compounds from readily available aldehyde, isocyanide and amidine building blocks. The reaction is driven by a wide range of catalysts and can be performed either under solvent or solvent-free conditions, or under microwave irradiation as heat source. The GBBR products can be used for the synthesis of a variety of more complex scaffolds via postmodification reactions. These include cyclization and nucleophilic substitution as well as further MCRs. The GBBR reaction has seen diverse applications in combinatorial and medicinal chemistry and its products are of great use in drug discovery. In this review, we summarize the efforts of the chemistry community in the progress and applications of GBBR since 1998. This review also includes some biological profiles and synthetic scopes of GBBR products. The component variations, postmodifications and secondary transformations will also be discussed throughout this review.

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“…In continuation of our recent studies on the modification and development of multicomponent reactions, and the design and synthesis of ferrocene‐containing magnetic nanocatalysts and Betti bases, herein we introduce a new 1,2,3‐triazolylferrocene‐containing ionic liquid nanocatalyst stabilized on silica‐coated Fe 3 O 4 ([Fe 3 O 4 @SiO 2 @Triazol‐Fc][HCO 3 ]). We also report a simple and efficient protocol for the three‐component one‐pot synthesis of pyran‐containing Betti base derivatives catalysed by [Fe 3 O 4 @SiO 2 @Triazol‐Fc][HCO 3 ] at room temperature (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of novel 1,2,3‐triazolylferrocene‐containing ionic liquid supported on Fe₃O₄ nanocatalyst in the synthesis of new pyran‐substituted Betti bases

Gholamhosseini-Nazari

Esmati

Safa

et al. 2019

Applied Organom Chemis

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A novel magnetic ferrocene‐labelled ionic liquid based on triazolium, [Fe3O4@SiO2@Triazol‐Fc][HCO3], has been synthesized and has been successfully introduced as a recyclable heterogeneous nanocatalyst. The catalytic activity of the novel magnetic nanoparticles was evaluated in the one‐pot three‐component synthesis of a wide variety of Betti bases. A simple, facile and highly efficient green method has been developed for the synthesis of kojic acid‐containing Betti base derivatives at room temperature. Additionally, this new protocol has notable advantages such as short reaction times, green reaction conditions, high yields and simple workup and purification steps. Also, the novel nanocatalyst could be easily recovered using an external magnetic field and reused for six consecutive reaction cycles without significant loss of activity. The newly synthesized nanocatalyst was characterized using Fourier transform infrared spectroscopy, X‐ray diffraction, energy‐dispersive X‐ray spectroscopy, field emission scanning electron microscopy, transmission electron microscopy and Brunauer–Emmett–Teller measurements.

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Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

Cited by 23 publications

References 47 publications

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

Synthesis and application of novel 1,2,3‐triazolylferrocene‐containing ionic liquid supported on Fe₃O₄ nanocatalyst in the synthesis of new pyran‐substituted Betti bases

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Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

Cited by 23 publications

References 47 publications

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media

Groebke–Blackburn–Bienaymé multicomponent reaction: emerging chemistry for drug discovery

Synthesis and application of novel 1,2,3‐triazolylferrocene‐containing ionic liquid supported on Fe3O4 nanocatalyst in the synthesis of new pyran‐substituted Betti bases

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Synthesis and application of novel 1,2,3‐triazolylferrocene‐containing ionic liquid supported on Fe₃O₄ nanocatalyst in the synthesis of new pyran‐substituted Betti bases