A Novel PPh<sub>3</sub> Mediated One-Pot Method for Synthesis of 3-Aryl or Alkyl 1,2-Benzisoxazoles

Chen, Guifang; Liu, Hong; Li, Shujia; Tang, Yu; Lu, Peiyao; Xu, Kan; Zhang, Yuanming

doi:10.1021/acs.orglett.7b00563

Cited by 7 publications

(5 citation statements)

References 49 publications

(27 reference statements)

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“…In the reactions using 15 mol‐% and 30 mol‐% of PPh 3 , a side product of biphenyl was isolated in yields of 8% and 4%, respectively, which reveals 15 mol‐% of PPh 3 can catalyze to give more biphenyl from bromobenzene than 30 mol‐% of PPh 3 . Although 15 mol‐% of PPh 3 can't promote the formation of salicyl alcohol, it could still catalyze bromobenzene to form biphenyl, which has been proved in our paper published recently, and thus results in lower yields of salicyl alcohol. In the reaction using 30 mol‐% of PPh 3 , bromobenzene can be catalyzed to form salicyl alcohol, and thus results in lower yields of biphenyl.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃

Zhang

Tang

et al. 2017

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A highly efficient and convenient Barbier‐Grignard‐type reaction to give salicyl alcohols and novel facile protocol to furnish unsymmetrical 9‐arylxanthenes using sodium salicylates and unactivated bromo‐hydrocarbons are described. Of total 21 synthesized compounds, 18 compounds containing 14 alcohols and 4 9‐arylxanthenes are new compounds. The products were provided in yields among 38–99%. The electronic and steric effects of bromo‐hydrocarbons on the reaction were discussed. Based on experimental results, a plausible mechanism concerning direct formation of salicyl alcohol from salicylate and PhMgBr with the promotion of PPh3 is proposed.

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Section: Resultsmentioning

confidence: 99%

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃

Zhang

Tang

et al. 2017

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“…Electrolysis products (10)(11)(12)(13)(14)(15)(16)(17)(18) were identified with the aid of gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and NMR spectroscopy. Products were characterized by comparison of their HRMS data, 1 H NMR spectra, and 13 C NMR spectra with those of authentic samples, either commercially available or chemically synthesized.…”

Section: Separation Isolation Identification and Quantitation Of Ementioning

confidence: 99%

“…However, several disadvantages, such as the need for expensive and relatively toxic catalysts, harsh reaction conditions, and multiple stages of synthesis, have limited the application of the homogeneous strategy for industrial‐scale processes. Moreover, chemically induced intramolecular cyclization culminates in Beckmann rearrangement and prevents formation of anthranil . On the other hand, heterogeneous catalyzed reactions rely on intramolecular cyclization, either in the form of deoxygenation or hydrogenation of o ‐nitrobenzaldehyde ( o ‐NBA).…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, chemically induced intramolecular cyclization culminates in Beckmann rearrangement and prevents formation of anthranil. [11] On the other hand, heterogeneous catalyzed reactions rely on intramolecular cyclization, either in the form of deoxygenation [12] or hydrogenation [13] of o-nitrobenzaldehyde (o-NBA). This approach leads to a very high yield and significant atom economy.…”

Section: Introductionmentioning

confidence: 99%

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Rapid and High‐Yield Electrosynthesis of Benzisoxazole and Some Derivatives

et al. 2018

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Cyclic voltammetry and controlled‐potential (bulk) electrolysis have been used to explore the electrochemical reduction of o‐nitrobenzaldehyde (o‐NBA) and 8 other aldehydes and ketones at glassy carbon cathodes in dimethylformamide containing various tetraalkylammonium tetrafluoroborate salts along with a proton donor (4‐chlorophenol). Cyclic voltammograms for reduction of o‐NBA exhibit three cathodic peaks attributable in succession to (a) one‐electron generation of the nitro radical‐anion, (b) three‐electron formation of the hydroxylamine, and (c) two‐electron production of benzisoxazole (anthranil). These findings have been employed to develop efficient controlled‐potential (bulk) electrosyntheses of the following compounds: benzisoxazole, methylbenzo[c]isoxazole, [1,3]dioxolo[4′,5′,4,5]benzo[1,2‐c]isoxazole, naphtho[2,3‐c]isoxazole, 6‐chlorobenzo[c]isoxazole, 6‐methoxybenzo[c]isoxazole, 3‐methyl‐benzo[c]isoxazole, 3‐isopropylbenzo[c]isoxazole, and 3‐phenylbenzo[c]isoxazole. In addition, we have examined the use of a variety of proton donors to optimize the production of the desired product, and we have been able to recover the proton donor at the conclusion of the electrosynthesis. In each case, the synthesized product was separated by means of normal phase chromatography and identified with the aid of NMR spectros‐copy, gas chromatography (GC), and gas chromatography‐mass spectrometry (GC‐MS). Isolated yields of the desired products range from 63 to 92 %. Moreover, our electrosyntheses are catalyst‐free, environmentally green, and rapid (∼30 min).

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“…Various protocols for the synthesis of 3-substituted benzisoxazoles have been reported so far [ 31 ]. Among others, catalytic cyclizations of 2-hydroxyaryl aldoximes and ketoximes [ 32 ] leading to the N–O bond formation through intramolecular Mitsunobu reaction [ 33 ] or by conversion of the hydroxyl group of the oximes to good, leaving groups followed by base-catalyzed ring-closure, are well-known procedures [ 3 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

et al. 2022

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Hybridization of steroids and other pharmacophores often modifies the bioactivity of the parent compounds, improving selectivity and side effect profile. In this study, estradiol and 3′-(un)substituted benzisoxazole moieties were combined into novel molecules by structural integration of their aromatic rings. Simple estrogen starting materials, such as estrone, estradiol and estradiol-3-methylether were used for the multistep transformations. Some of the heterocyclic derivatives were prepared from the estrane precursor by a formylation or Friedel–Crafts acylation—oximation—cyclization sequence, whereas others were obtained by a functional group interconversion strategy. The antiproliferative activities of the synthesized compounds were assessed on various human cervical, breast and prostate cancer cell lines (HeLa, MCF-7, PC3, DU-145) and non-cancerous MRC-5 fibroblast cells. Based on the primary cytotoxicity screens, the most effective cancer-selective compounds were selected, their IC50 values were determined and their apoptosis-inducing potential was evaluated by quantitative real-time PCR. Pharmacological studies revealed a strong structure–function relationship, where derivatives with a hydroxyl group on C-17 exhibited stronger anticancer activity compared to the 17-acetylated counterparts. The present study concludes that novel estradiol-benzisoxazole hybrids exert remarkable cancer cell-specific antiproliferative activity and trigger apoptosis in cancer cells.

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A Novel PPh₃ Mediated One-Pot Method for Synthesis of 3-Aryl or Alkyl 1,2-Benzisoxazoles

Cited by 7 publications

References 49 publications

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃

Rapid and High‐Yield Electrosynthesis of Benzisoxazole and Some Derivatives

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

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A Novel PPh3 Mediated One-Pot Method for Synthesis of 3-Aryl or Alkyl 1,2-Benzisoxazoles

Cited by 7 publications

References 49 publications

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh3

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh3

Rapid and High‐Yield Electrosynthesis of Benzisoxazole and Some Derivatives

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

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A Novel PPh₃ Mediated One-Pot Method for Synthesis of 3-Aryl or Alkyl 1,2-Benzisoxazoles

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃

Preparation of Salicyl Alcohols and 9‐Arylxanthenes Using Sodium Salicylates and Bromo‐Hydrocarbons Mediated by PPh₃