Niobium Pentachloride Mediated (Hetero)aromatic Aldehyde Friedel–Crafts Hydroxyalkylation with Arenes: An Efficient Strategy to Synthesize Triarylmethanes

Rodrigues, Shirley Muniz Machado; Previdi, Daniel; Baviera, Giovanni S.; Matias, Alexandre A.; Donate, Paulo Marcos

doi:10.1055/s-0037-1610727

Cited by 6 publications

(5 citation statements)

References 19 publications

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“…On the basis of the above-mentioned data, DMF volumes were studied. After diluting the reaction concentration from 1 mL to 5 mL, a slightly lower yield (78%) was obtained (entry 11). Under solvent-free conditions, however, a neat solution system provided similar yields (82%, entry 12).…”

Section: Paper Synthesismentioning

confidence: 99%

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confidence: 99%

“…Traditionally, the Friedel-Crafts reaction and Baeyer condensation have been two of the most commonly employed tools for the formation of TRAMs in the presence of different promoters. Several promoters have been reported, as shown in Scheme 1, including protic acid (TsOH, 7 TfOH 8 ), Lewis acid (FeCl 3 , 9 TiCl 4 , 10 NbCl 5 , 11 SbCl 3 , 12 AlCl 3 , 13 AuCl 3 , 14 CuCl 2 , 15 SnCl 4 , 16 ZrOCl 2 17 ), acidic polymer (NKC-9, 18 Amberlyst-15, 19 Nafion-H 20 ), oxidant (NaICl 2 , 21 I 2 22 ), clay (K10), 23 ionic liquid, 24 microwave irradiation, and sonication. 25 Scheme 1 Synthetic routes of triarylmethanes (TRAMs)…”

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confidence: 99%

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Gram-Scale Synthesis of Substituted Triarylmethanes

2022

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A high-yield, open-vessel route for the facile-operational, gram-scale synthesis of functionalized triarylmethanes (TRAMs) is described via silica-coated magnetic nanoparticles of modified polyphosphoric acid (NiFe2O4@SiO2-PPA)-mediated intermolecular Friedel–Crafts reaction of substituted aryl aldehydes with 2 equivalents of oxygenated arenes under environmentally friendly reaction conditions. Among the overall reaction process, only water was generated as the by-product. Various reaction conditions are investigated for efficient transformation.

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Section: Paper Synthesismentioning

confidence: 99%

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Gram-Scale Synthesis of Substituted Triarylmethanes

2022

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“…Thus, the decomposition of NbCl 5 assisted the formation of the desired m-CUR product. A variety of applications of NbCl 5 in organic synthesis have been reported, for example, in Diels-Alder reactions, multicomponent reactions (MCR), and one-pot reactions, among others [35,36]. In this context, the use of NbCl 5 consists of a new alternative to Claisen-Schmidt condensation.…”

Section: Synthesis and Structural Characterization Of The Monoketone ...mentioning

confidence: 99%

Monoketonic Curcuminoid-Lidocaine Co-Deliver Using Thermosensitive Organogels: From Drug Synthesis to Epidermis Structural Studies

et al. 2022

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Organogels (ORGs) are remarkable matrices due to their versatile chemical composition and straightforward preparation. This study proposes the development of ORGs as dual drug-carrier systems, considering the application of synthetic monoketonic curcuminoid (m-CUR) and lidocaine (LDC) to treat topical inflammatory lesions. The monoketone curcuminoid (m-CUR) was synthesized by using an innovative method via a NbCl5–acid catalysis. ORGs were prepared by associating an aqueous phase composed of Pluronic F127 and LDC hydrochloride with an organic phase comprising isopropyl myristate (IPM), soy lecithin (LEC), and the synthesized m-CUR. Physicochemical characterization was performed to evaluate the influence of the organic phase on the ORGs supramolecular organization, permeation profiles, cytotoxicity, and epidermis structural characteristics. The physico-chemical properties of the ORGs were shown to be strongly dependent on the oil phase constitution. Results revealed that the incorporation of LEC and m-CUR shifted the sol-gel transition temperature, and that the addition of LDC enhanced the rheological G′/G″ ratio to higher values compared to original ORGs. Consequently, highly structured gels lead to gradual and controlled LDC permeation profiles from the ORG formulations. Porcine ear skin epidermis was treated with ORGs and evaluated by infrared spectroscopy (FTIR), where the stratum corneum lipids were shown to transition from a hexagonal to a liquid crystal phase. Quantitative optical coherence tomography (OCT) analysis revealed that LEC and m-CUR additives modify skin structuring. Data from this study pointed ORGs as promising formulations for skin-delivery.

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“…Recently, we have published a method for synthesizing triarylmethanes from arenes and aromatic aldehydes mediated by niobium(V) chloride. 18 As part of our interest in developing new synthetic methodologies that use NbCl 5 , here we report a rapid and efficient strategy to synthesize many substituted 9-anthraldehydes in excellent yields through a direct Bradsher-type reaction of easily prepared triarylmethanes and Cl 2 CHOMe.…”

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confidence: 99%