Synthesis and Fluorescent Properties of a New Class of Heterocycles of Isoindole Fused Imidazoles with Phenolic Subunits

Das, Suven; Fröhlich, Roland; Pramanik, Animesh

doi:10.1021/ol061520n

Cited by 60 publications

(16 citation statements)

References 18 publications

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“…The title compound 1-(2-hydroxy-5-chloro-phenyl)-3,5-dioxo-1H-imidazo-[3,4-b] isoindole (ADCL) was synthesized as was reported in the literature 43 . The surfactants 6 sodium dodecyl sulfate (SDS), cetyltrimethyl ammonium bromide (CTAB), Triton X-100 (TX 100) and Pluronic triblock copolymers P123 have been purchased from Sigma Chemical Co. and were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Modulation of Excited State Proton Transfer Dynamics of a Lactim–Lactam Tautomeric System in Different Block Copolymer–Surfactant Aggregates

2015

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The proton transfer (PT) process in 1-(2-hydroxy-5-chloro-phenyl)-3,5-dioxo-1H-imidazo-[3,4-b]isoindole (ADCL) has been studied in three different copolymer-surfactant supramolecular assemblies prepared in aqueous 1% P123 triblock copolymer micellar solution with varying concentrations of surfactants (sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), and triton-X-100 (TX 100)). The aim of the present study is to monitor the modulation of the PT process by changing the degree of micellar hydration inside the P123 micelle with the addition of the three different surfactants (two ionic and one non ionic), that is, in P123-surfactant aggregates. Besides, a comparative study has been done with these results with those in water, pure P123 micellar medium and three different surfactants medium. The micropolarity measurement and time-resolved fluorescence anisotropic measurements have been performed to evaluate the binding location of the probe (ADCL) in the three different copolymer-surfactant supramolecular assemblies. It is found that the micropolarity at the binding site of the molecule in the various environments largely influences the PT rate of ADCL. The PT rate is found to be the slowest in the P123 medium and in P123-surfactant aggregates the rate becomes faster as the micropolarity around the binding locations of the molecule in these aggregates is higher in comparison to that in P123 micelle.

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Section: Methodsmentioning

confidence: 99%

Modulation of Excited State Proton Transfer Dynamics of a Lactim–Lactam Tautomeric System in Different Block Copolymer–Surfactant Aggregates

2015

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“…74,160 With this in mind, Pramanik and co-workers reported refluxing 206 with urea in acetic acid (one pot reaction) to produce isoindole fused imidazoles with phenolic subunits 207 (Scheme 60). 271 It was observed that in aprotic solvent, they show high fluorescent properties, but in protic polar solvent, fluorescent intensity decreases.…”

Section: Scheme 57 Synthesis Of Indeno[12-d]imidazolidin-2-iminium mentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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“…SSA, a product that is easily synthesized from silica gel and chlorosulfonic acid [26], was observed to improve the reactivity and selectivity in carbon–carbon bond-formation reactions [27–28], in cycloaddition reactions [29–30], in protection–deprotection reactions of multistep syntheses [31–33], in esterifications [34] and in syntheses of heterocycles [35]. Since we are actively involved in the synthesis of biologically important heterocycles [36–42], we wish to report herein a green methodology for the construction of pyrrole-fused isocoumarins, which uses SSA as a solid-supported acid catalyst under solvent-free conditions (Scheme 1, present work).…”

Section: Introductionmentioning

confidence: 99%

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

Pathak¹,

Debnath²,

Pramanik

2013

Beilstein J. Org. Chem.

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SummaryA convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.

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Synthesis and Fluorescent Properties of a New Class of Heterocycles of Isoindole Fused Imidazoles with Phenolic Subunits

Cited by 60 publications

References 18 publications

Modulation of Excited State Proton Transfer Dynamics of a Lactim–Lactam Tautomeric System in Different Block Copolymer–Surfactant Aggregates

Modulation of Excited State Proton Transfer Dynamics of a Lactim–Lactam Tautomeric System in Different Block Copolymer–Surfactant Aggregates

Ninhydrin in synthesis of heterocyclic compounds

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

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