Oxidative Amidation of Aromatic Ethers Catalyzed by Rhodium Acetate

Deng, Yanan; Xie, Jiang-Ping; Zhang, Wen; Yin, Ping; Yu, Jing; He, Ling

doi:10.1002/chem.201102303

Cited by 15 publications

(6 citation statements)

References 64 publications

(27 reference statements)

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“…He and co‐workers recently described the formation of quinone derivatives and not the expected benzomorpholines in a rhodium‐catalyzed reaction with the same tethered phenol derivatives (Figure 3). 25 Our simple approach described herein can provide the starting materials for this reaction in one step from the corresponding aryllithiums. We reasoned, however, that the sought‐after benzomorpholine derivatives could be easily obtained through the radical rather than metal‐catalyzed cyclization reaction of N‐centered radicals.…”

Section: Resultsmentioning

confidence: 99%

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Javorskis

Sriubaitė

Bagdžiūnas

et al. 2015

Chemistry A European J

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A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance.

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Section: Resultsmentioning

confidence: 99%

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Javorskis

Sriubaitė

Bagdžiūnas

et al. 2015

Chemistry A European J

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“…The formations reaction of 1a and 2a were taken as an example for optimization of reaction conditions of the oxidative amination using the previous work as ref. 19 and 31 The results (Table 1) show that copper(II), rhodium(II) and ruthenium(II) could be used as a catalyst for the amination of aromatic ether 5 and 6 . Other metal complexes, such as those of Mn(II), Co(II) and Fe(II) displayed poor catalytic activities.…”

Section: Resultsmentioning

confidence: 99%

Copper salt-catalyzed formation of a novel series of triazole–spirodienone conjugates with potent anticancer activity

Wang

Deng

et al. 2017

RSC Adv.

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Copper salt-catalyzed oxidative amination resulted in the formation of a novel series of triazole– spirodienone conjugates, 4-triazolyl-1-oxa-4-azaspiro[4,5]deca-6,9-dien-3,8-diones and 4-triazolyl-1-oxa-4-azaspiro[4,5]deca-6,9-dien-8-ones. A single crystal of compound 1p among them was grown and analyzed by X-ray crystallography. These compounds were evaluated for their antiproliferative activities against MDA-MB-231, HeLa, A549 and MCF-7 cell lines. Most of them showed moderate to high anticancer potency in the four cancer cell lines. The discovery of the triazole–spirodienone conjugates as cytotoxic agents against cancer cells may open up a new field in which these novel small molecules could be further explored as promising anticancer agents.

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“…O-Alkylation of phenols with 4 formed the intermediates 5. Rhodium acetate-catalyzed oxidation and concomitant intramolecular amidation of 5 resulted in the formation of 6 by bis(trifluoroacetoxy)iodobenzene under mild conditions [23]. The copper-catalyzed click reaction of 6 with the azides [31,32] produced the derivatives 7.…”

Section: Chemical Synthesismentioning

confidence: 99%

“…Previously, we have hybridized these pharmacologically active structural elements (sulfonamide, quinone, and spirocyclic moieties) and obtained a series of benzenesulfonylazaspirodienones. [23]. The preliminary screening proved that these compounds have a certain inhibitory effect on cancer cell lines [24].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

et al. 2020

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Many sulfonamides show anticancer activity. Based on benzenesulfonylazaspirodienone (HL-X9) identified in our previous work, we optimized the lead compound for better efficacy, thereby synthesizing a series of novel 4-(aromatic sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-one derivatives through a key step of metal-catalyzed cascade cyclization. The preliminary antiproliferative tests have shown that the anticancer activities of acetyl-protected mannose-linked sulfonylazaspirodienone derivatives (7i–7l) have been greatly improved. Among them, 7j is the most potent derivative, with IC50 values of 0.17 µM, 0.05 µM, and 0.07 µM for A549, MDA-MB-231, and HeLa cell lines, respectively. Flow cytometry analysis shows that 7j arrests MDA-MB-231 cells in the G2/M phase and has a certain effect on the apoptosis of MDA-MB-231 cells. In addition, the acute toxicity of 7j was lower than that of adriamycin.

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Oxidative Amidation of Aromatic Ethers Catalyzed by Rhodium Acetate

Cited by 15 publications

References 64 publications

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

N‐Protected 1,2‐Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether

Copper salt-catalyzed formation of a novel series of triazole–spirodienone conjugates with potent anticancer activity

Design, Synthesis, and Antitumor Activity of a Series of Novel 4-(Aromatic Sulfonyl)-1-oxa-4-azaspiro[4.5]deca-6,9-dien-8-ones

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