A Novel Synthesis of Indandiones Using the HOF·CH<sub>3</sub>CN Complex

Dayan, Sharon; Almog, Joseph; Khodzhaev, O.F.; Rozen, Shlomo

doi:10.1021/jo972088d

Cited by 20 publications

(13 citation statements)

References 18 publications

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“…Thus, 4-vinylpyridine (69) was converted in 70 % yield to the corresponding N-oxide without affecting the olefin. Similarly dioctyl methylamine (78) was converted in 95 % yield to its N-oxide, an important industrial chemical, which was a subject of several patents. Tertiary aliphatic and alicyclic amines have proved to be excellent substrates as well.…”

Section: Reactions Around Tertiary Nitrogen Atomsmentioning

confidence: 99%

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Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Rozen

2005

Eur J Org Chem

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At present, HOF·CH3CN complex is the best oxygen transfer agent that chemistry has to offer. It is readily made by passing dilute fluorine through aqueous acetonitrile and does not require any isolation or purification. It is stable in aqueous acetonitrile solution for a few hours at room temperature, providing ample opportunities for various reactions. Epoxidation of regular olefins as well as of very electron‐depleted ones proceeds smoothly. HOF·CH3CN transfer oxygen also to heteroatoms, especially sulfur and nitrogen. Even very electron‐depleted sulfides such as RfSAr that are very difficult to oxidize, are converted into the respective sulfones in a matter of minutes. On the other hand, since the reaction conditions are very mild, the reagent can oxidize various thiophenes and amino acids to the corresponding S,S‐dioxides and α‐nitro acid derivatives. HOF·CH3CN was also instrumental in ending the 50 years quest for making the elusive 1,10‐phenanthroline N,N‐dioxide and for the novel transformation of azides to nitro derivatives. The use of BrF3 for making symmetric esters and of tBuOF as an electrophilic tert‐butoxylation agent is also mentioned. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Reactions Around Tertiary Nitrogen Atomsmentioning

confidence: 99%

“…[78] Most police departments use ninhydrin (114) and 1,8-diazafluorene-9-one (115) for the visualization of latent fingerprints on paper items. [78] Most police departments use ninhydrin (114) and 1,8-diazafluorene-9-one (115) for the visualization of latent fingerprints on paper items.…”

Section: Hydroxylations α To Ketonesmentioning

confidence: 99%

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Rozen

2005

Eur J Org Chem

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“…[12] It has been used for the ahydroxylation of carbonyl compounds and has helped to synthesize some previously impossible indandiones for visualization of fingerprints. [14] Finally HOF´CH 3 CN has been used successfully to convert tertiary amines into their N-oxides in very good yields. [15] We therefore tried its reaction with 1,10phenanthroline.…”

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confidence: 99%

At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN

Rozen

Dayan

1999

Angewandte Chemie International Edition

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For more than 50 years the synthesis of 1,10-phenanthroline-N,N'-dioxide (2) has been sought. The reason for the failure of all the earlier attempts is that the limited space in the bay area of the starting material 1,10-phenanthroline (1) cannot accommodate two oxygen atoms. The oxidation has now been achieved with the oxygen-transfer agent HOF small middle dotCH(3)CN, and X-ray studies have revealed that the product is not planar but is a new type of helicene-in this way the "space problem" for the two oxygen atoms has been solved.

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“…During the last few years, a series of indanedione compounds were synthesized [7] and reported in the literature for their fluorescent properties [8,9]. Although substituted indane-1,3-dione derivatives have been used in the fields of medicine [10] and biology [11], literature data on their chemical and physical interactions with proteins is scarce [12,13], and no chemical and physical studies of their interaction with immunoglobulins, and their applicability as fluorescent labels were found.…”

Section: Introductionmentioning

confidence: 99%

2-(2-Hydroxy-5-nitrobenzylidene)-1,3-indanedione versus Fluorescein Isothiocyanate in Interaction with Anti-hFABP Immunoglobulin G1: Fluorescence Quenching, Secondary Structure Alteration and Binding Sites Localization

Stan

Mihailescu

Savin

et al. 2013

IJMS

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The first step in determining whether a fluorescent dye can be used for antibody labeling consists in collecting data on its physical interaction with the latter. In the present study, the interaction between the 2-(2-hydroxy-5-nitrobenzylidene)-1,3-indanedione (HNBID) dye and the IgG1 monoclonal mouse antibody anti-human heart fatty acid binding protein (anti-hFABP) has been investigated by fluorescence and circular dichroism spectroscopies and complementary structural results were obtained by molecular modeling. We have determined the parameters characterizing this interaction, namely the quenching and binding constants, classes of binding sites, and excited state lifetimes, and we have predicted the localization of HNBID within the Fc region of anti-hFABP. The key glycosidic and amino acid residues in anti-hFABP interacting with HNBID have also been identified. A similar systematic study was undertaken for the well-known fluorescein isothiocyanate fluorophore, for comparison purposes. Our results recommend HNBID as a valuable alternative to fluorescein isothiocyanate for use as a fluorescent probe for IgG1 antibodies.

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A Novel Synthesis of Indandiones Using the HOF·CH₃CN Complex

Cited by 20 publications

References 18 publications

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN

2-(2-Hydroxy-5-nitrobenzylidene)-1,3-indanedione versus Fluorescein Isothiocyanate in Interaction with Anti-hFABP Immunoglobulin G1: Fluorescence Quenching, Secondary Structure Alteration and Binding Sites Localization

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A Novel Synthesis of Indandiones Using the HOF·CH3CN Complex

Cited by 20 publications

References 18 publications

Elemental Fluorine and HOF·CH3CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH3CN in Service of General Organic Chemistry

At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN

2-(2-Hydroxy-5-nitrobenzylidene)-1,3-indanedione versus Fluorescein Isothiocyanate in Interaction with Anti-hFABP Immunoglobulin G1: Fluorescence Quenching, Secondary Structure Alteration and Binding Sites Localization

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A Novel Synthesis of Indandiones Using the HOF·CH₃CN Complex

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry

Elemental Fluorine and HOF·CH₃CN in Service of General Organic Chemistry