Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene

Tao, Jason; Tuck, Tina N.; Murphy, Graham K.

doi:10.1055/s-0035-1561283

Cited by 6 publications

(3 citation statements)

References 7 publications

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“…The reaction of 1-(naphthalen-2-yl)ethan-1-one (11) with pyrimidine-5carbaldehyde in the presence of Ba(OH) 2 afforded α-H chalcone 9 in a 55% yield (Scheme 1). The ketone 11 reacted with dimethyl carbonate, as described, to provide the methyl 3oxopropanoate 12 [28], whose reaction with pyrimidine-5-carbaldehyde resulted in the α-COOCH 3 chalcone 13. Reaction of the ester 12 with NH 3 /dioxane at 110 • C [29] led to the amide 14 that was further transformed into the chalcone 15.…”

Section: Synthesismentioning

confidence: 99%

“…Following general procedure B, a solution of methyl 3-(naphthalen-2-yl)-3-oxopropanoate (12) [28] (58 mg, 0.25 mmol), pyrimidine-5-carboxaldehyde (80 mg, 0.70 mmol) and piperidine (13 µL, 0.13 mmol) in glacial acetic acid (1 mL) was stirred at 100 • C overnight and evaporated. The residue was purified by CCTLC in the Chromatotron (DCM/ethyl acetate, 12:1) to yield 32 mg (40%) of 13 as a white solid.…”

Section: Chemistry Proceduresmentioning

confidence: 99%

“…Scheme 1. Reagents and conditions: (a) pyrimidine-5-carbaldehyde, Ba(OH)2, methanol/water, rt, 2 h, 55% yield; (b) as described in[28]: dimethyl carbonate, NaH, 1,4-dioxane, 70 °C, 3.5 h; (c) pyrimidine-5-carbaldehyde, piperidine, AcOH, 70-100 °C, 2-48 h, 30-40% yield; (d) NH3, 1,4-dioxane, 110 °C, 16 h, 34% yield; (e) as described in[30]: propionyl chloride, AlCl3, 1,2-DCE, rt, 16 h; (f) as described in[32]: acetonitrile, NaH, toluene, 110 °C, 16 h.…”

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Inhibition of XPO-1 Mediated Nuclear Export through the Michael-Acceptor Character of Chalcones

et al. 2021

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The nuclear export receptor exportin-1 (XPO1, CRM1) mediates the nuclear export of proteins that contain a leucine-rich nuclear export signal (NES) towards the cytoplasm. XPO1 is considered a relevant target in different human diseases, particularly in hematological malignancies, tumor resistance, inflammation, neurodegeneration and viral infections. Thus, its pharmacological inhibition is of significant therapeutic interest. The best inhibitors described so far (leptomycin B and SINE compounds) interact with XPO1 through a covalent interaction with Cys528 located in the NES-binding cleft of XPO1. Based on the well-established feature of chalcone derivatives to react with thiol groups via hetero-Michael addition reactions, we have synthesized two series of chalcones. Their capacity to react with thiol groups was tested by incubation with GSH to afford the hetero-Michael adducts that evolved backwards to the initial chalcone through a retro-Michael reaction, supporting that the covalent interaction with thiols could be reversible. The chalcone derivatives were evaluated in antiproliferative assays against a panel of cancer cell lines and as XPO1 inhibitors, and a good correlation was observed with the results obtained in both assays. Moreover, no inhibition of the cargo export was observed when the two prototype chalcones 9 and 10 were tested against a XPO1-mutated Jurkat cell line (XPO1C528S), highlighting the importance of the Cys at the NES-binding cleft for inhibition. Finally, their interaction at the molecular level at the NES-binding cleft was studied by applying the computational tool CovDock.

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Section: Synthesismentioning

confidence: 99%

Section: Chemistry Proceduresmentioning

confidence: 99%

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Inhibition of XPO-1 Mediated Nuclear Export through the Michael-Acceptor Character of Chalcones

et al. 2021

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ChemInform Abstract: Geminal Dichlorination of Phenyliodonium Ylides of β‐Dicarbonyl Compounds Through Double Ligand Transfer from (Dichloroiodo)‐benzene.

2016

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7−8 years, between 2016 and 2024.

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Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene

Cited by 6 publications

References 7 publications

Inhibition of XPO-1 Mediated Nuclear Export through the Michael-Acceptor Character of Chalcones

Inhibition of XPO-1 Mediated Nuclear Export through the Michael-Acceptor Character of Chalcones

ChemInform Abstract: Geminal Dichlorination of Phenyliodonium Ylides of β‐Dicarbonyl Compounds Through Double Ligand Transfer from (Dichloroiodo)‐benzene.

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

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