Synthesis of 1,2-Benzisoxazole 2-Oxides

Kociolek, Martin G.; Hoermann, Olivia

doi:10.1080/00397911.2011.563451

Cited by 10 publications

(15 citation statements)

References 20 publications

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“…[12] Electrochemical measurements All electrochemical measurements were performed at room temperature using a single-compartment glass cell and a CH Instruments model 842C Series Electrochemical Analyzer (CH Instruments, Austin, TX). The design of the electrochemical cell was reported previously.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical reduction of 3‐phenyl‐1,2‐benzisoxazole 2‐oxide on boron‐doped diamond

Kociolek

Bennett

Casbohm

2014

J of Physical Organic Chem

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aThe bioreduction of N-oxide compounds is the basis for the mode of action of a number of biologically active molecules. These compounds are thought to act by forming a reactive oxygen species through an intracellular reduction and subsequent redox cycling process within the organism. With these results in mind, the preliminary investigation into the electrochemical reduction of the benzisoxazole 2-oxide ring system was undertaken, with the thought that this class of compounds would reduce in a similar fashion to other N-oxide heterocycles. The electrochemical reduction of 3-phenyl-1,2-benzisoxazole 2-oxide on boron-doped diamond was studied using cyclic and square wave voltammetry as well as controlled potential electrolysis and HPLC for qualitative identification of the reaction products. It was found that the reduction proceeded with an initial quasi-reversible one-electron reduction followed by the very fast cleavage of either the endocyclic or exocyclic N-O bond. Subsequent electron transfer and protonation resulted in an overall two-electron reduction and formation of the 2-hydroxyaryl oxime and benzisoxazole. These results are analogous to those observed in the electrochemical reduction of other heterocyclic N-oxides albeit the reduction of the benzisoxazole N-oxides takes place at a more negative potential. However, these encouraging results warrant further investigation into the reduction potential of substituted benzisoxazole N-oxides as well as to elucidate and characterize the nature of the intermediate species involved.

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Section: Methodsmentioning

confidence: 99%

Electrochemical reduction of 3‐phenyl‐1,2‐benzisoxazole 2‐oxide on boron‐doped diamond

Kociolek

Bennett

Casbohm

2014

J of Physical Organic Chem

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“…The benzisoxazole 2-oxides under investigation were synthesized as previously reported. [20] The appropriate acetophenones and benzophenones were converted to the corresponding oximes by treatment with hydroxylamine hydrochloride and cyclized with iodobenzene diacetate (Scheme 1). Compounds 1a-h and 1l gave 1 H and 13 C NMR spectra identical to those previously reported in the literature.…”

Section: Preparation Of Benzisoxazole 2-oxidesmentioning

confidence: 99%

“…Compounds 1a-h and 1l gave 1 H and 13 C NMR spectra identical to those previously reported in the literature. [20][21][22] Compounds 1j and 1k were characterized by NMR and gave appropriate CHN elemental analysis.…”

Section: Preparation Of Benzisoxazole 2-oxidesmentioning

confidence: 99%

Benzisoxazole 2‐oxides as novel UV absorbers and photooxidation inhibitors

Kociolek

Casbohm

2013

J of Physical Organic Chem

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Compounds with strong absorptions in the ultraviolet (UV) region of the spectrum, particularly the UVA and UVB, have seen much interest as UV screeners or absorbers in a wide variety of commercial products. A series of benzisoxazole 2-oxides have been synthesized and characterized by UV-vis spectroscopy. A number of derivatives have been shown to posses moderate to strong molar absorption coefficients in the UVB range (ca. 300 nm), the strongest being those derived from benzophenones. Three other derivatives containing additional electron withdrawing groups showed strong molar absorption coefficients in the UVA (ca. 340 nm). Solvent effects on the parent derivatives show changes in the molar absorption coefficients with little changes in the λ max values. Preliminary studies of these compounds as potential additives to prevent photooxidation of polystyrene showed considerable inhibition of polymer degradation with the parent unsubstituted benzisoxazole 2-oxide compounds being the most effective.

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“…The cyclization reactions of oximes using hypervalent iodine(III) reagents can proceed with various nucleophiles, such as alkenes, [73][74][75][76] alcohols, [77][78][79][80][81] or amines, 67,82 within the molecule to produce the respective cyclic compounds. For example, Aggarwal and co-workers have reported an efficient synthesis of 2,3-diphenylquinoxaline-1-oxides 56 from benzyl--arylimino oximes 55 using DIB (Scheme 17).…”

Section: Reactions Of Ketoximes Using Hypervalent Iodine Reagentsmentioning

confidence: 99%

“…Reactions of ketoximes in which an N-O bond is formed, giving isoxazole N-oxide derivatives, have been reported. [77][78][79][80] Effective procedures for the preparation of various isoxazole N-oxides from ketoximes have been developed by several research groups. Yao and co-workers have reported the Koser's reagent-induced oxidative heterocyclization reactions of ketoximes in water or methanol producing the corresponding isoxazole N-oxides in good yields.…”

Section: Reactions Of Ketoximes Using Hypervalent Iodine Reagentsmentioning

confidence: 99%

Oxidative cyclizations of oximes using hypervalent iodine reagents

Yoshimura

Zhdankin²

2017

Arkivoc

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This account overviews oxidative cyclization reactions of aldoximes or ketoximes promoted by hypervalent iodine reagents. The oxidation of aldoximes by iodine(III) compounds generates nitrile oxides which can further react with appropriate substrates via intermolecular or intramolecular 1,3-dipolar cycloaddition reactions leading to a variety of nitrogen and oxygen heterocycles. Hypervalent iodine reagents can also react with ketoximes producing the corresponding heterocyclic products via intramolecular cyclization reactions. Recently, the oxidative cyclization reactions of aldoximes have been realized under catalytic conditions mediated by hypervalent iodine active species.

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Synthesis of 1,2-Benzisoxazole 2-Oxides

Cited by 10 publications

References 20 publications

Electrochemical reduction of 3‐phenyl‐1,2‐benzisoxazole 2‐oxide on boron‐doped diamond

Electrochemical reduction of 3‐phenyl‐1,2‐benzisoxazole 2‐oxide on boron‐doped diamond

Benzisoxazole 2‐oxides as novel UV absorbers and photooxidation inhibitors

Oxidative cyclizations of oximes using hypervalent iodine reagents

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