Polymer‐Supported Ferric Chloride as a Heterogeneous Catalyst for Chemoselective Deprotection of Acetonides.

Chari, M. Adharvana; Syamasundar, K. V.

doi:10.1002/chin.200534252

Cited by 3 publications

(3 citation statements)

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“…The reports relating to the syntheses of 3,4‐dihydroquinoxaline‐2‐ amines appeared in the literature are very limited andinclude the use of PTSA, [106] ceric ammonium nitrate (CAN), [107] Fe(ClO4) 3 , [84] and EDTA [108] as non‐recyclable catalysts. The use of heterogeneous catalysts [109–111] especially amberlyst‐15 [112–115] in organic synthesis has received considerable interest because of operational simplicity, enhanced reaction rates, greater selectivity, recyclability and reusability.…”

Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

Advances in Isocyanide‐Based Multicomponent Synthesis of Quinoxaline Scaffolds

Agarwal,

Verma,

Pathak

et al. 2023

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The present review article includes recent advances in the synthesis of structurally and functionally diversified quinoxalines‐drug‐like small molecules with molecular complexity. We have extended our efforts to include the research work concerning the isocyanide‐based multicomponent reactions. The synthetic methods included in the present review article will provide an access for a diverse range of natural product mimetic scaffolds with the use of isocyanide‐.based combinatorial synthesis. These isocyanide based reactions will be significant for the synthesis of complex bioactive natural products and potential synthetic pharmaceuticals. The present review will contribute considerably to the organic syntheses and particularly drug discovery research including pharmaceutical and medicinal chemistry. Academically, the present review article will be interesting for the researchers engaged in design and development of isocyanide‐based organic transformations. Moreover, we hope that the isocyanide‐based multicomponent reactions will find major applications in industrially significant organic transformations and to develop new synthetic routes to facilitate the incorporation of heterocyclic substructures into pharmaceutically active molecules.

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Section: Synthesis Of Quinoxalinesmentioning

confidence: 99%

Advances in Isocyanide‐Based Multicomponent Synthesis of Quinoxaline Scaffolds

Agarwal,

Verma,

Pathak

et al. 2023

ChemistrySelect

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“…Fe(III) has the ability to catalyze the diacrylate cross-linking reaction, but separating it from PEI post-synthesis is difficult due to PEI’s metal chelating potential (16). By incorporating a polymer support, the PVP(Fe(III)) provides a low-cost, heterogeneous catalyst that allows easy catalyst recovery (17). As a result, this alternative synthesis scheme provides a more controllable PEI cross-linking method and D.PEIs with wider range of molecular weights, as well as enhanced transfection properties.…”

Section: Introductionmentioning

confidence: 99%

The Effects of PVP(Fe(III)) Catalyst on Polymer Molecular Weight and Gene Delivery Via Biodegradable Cross-Linked Polyethylenimine

et al. 2011

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Purpose Crosslinked, degradable derivatives of low-molecular-weight polyethylenimine (PEI) are relatively efficient and non-cytotoxic gene delivery agents. To further investigate these promising materials, a new synthetic approach was developed using a poly(4-vinylpyridine)-supported Fe(III) catalyst (PVP(Fe(III))) that provides more facile synthesis and enhanced control of polymer molecular weight. Methods Biodegradable polymers (D.PEI) comprising 800-Da PEI crosslinked with 1,6-hexanediol diacrylate and exhibiting molecular weights of 1.2, 6.2, and 48 kDa were synthesized utilizing the PVP(Fe(III)) catalyst. D.PEI/DNA polyplexes were characterized using gel retardation, ethidium bromide exclusion, heparan sulfate displacement, and dynamic light scattering. In vitro transfection, cellular uptake, and cytotoxicity of the polyplexes were tested in human cervical cancer cells (HeLa) and human breast cancer cells (MDA-MB-231). Results D.PEIs tightly complexed plasmid DNA and formed 320- to 440-nm diameter polyplexes, similar to those comprising non-degradable, 25-kDa, branched PEI. D.PEI polyplexes mediated 2- to 5-fold increased gene delivery efficacy compared to 25-kDa PEI and exhibited 20% lower cytotoxicity in HeLa and no toxicity in MDA-MB-231. In addition, 2- to 7-fold improved cellular uptake of DNA was achieved with D.PEI polyplexes. Conclusions PVP(Fe(III)) catalyst provided a more controlled synthesis of D.PEIs, and these materials demonstrated improved in vitro transfection efficacy and reduced cytotoxicity.

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“…Many of the synthesis methods of 1,5-benzodiazepines suffer from one or more limitations, such as long reaction times, occurrence of side reactions [13], severe reaction conditions, low yields, use of corrosive chemicals (e.g., HCl gas, trifluoroacetic acid) and hazardous reagents (e.g., pyridine, piperidine, halogenated hydrocarbon), high-boiling solvent (e.g., dimethylformamide), and tedious work-up procedures. Catalysts such as BF 3 -Et 2 O [14], NaBH 4 [15], ceric ammonium nitrate [16], PPA/SiO 2 [17], MgO/POCl 3 [18], Yb(OTf) 3 [19], AcOH under microwave conditions [20], NBS [21], polymer-supported FeCl 3 Sc(OTf) 3 [22], and ionic liquids [23] have been used to improve reaction efficiency. The main disadvantages of these catalysts are that they get lost in the work-up procedure, cannot be recovered or reused, and are highly toxic and expensive [24].…”

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confidence: 99%