17512-70-8

Usage

Uses

Used in Organic Synthesis:
2-fluoro-N-hydroxybenzamide is utilized as a key intermediate in organic synthesis for the construction of complex organic molecules. Its presence of a fluorine atom and hydroxyl group on the benzene ring allows for a variety of chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-fluoro-N-hydroxybenzamide is employed as a starting material for the development of new drugs. Its unique structure and properties make it a candidate for the design of innovative therapeutic agents. Researchers are investigating its potential biological activities, which may lead to the discovery of new treatments for various diseases.
Used in Drug Development:
2-fluoro-N-hydroxybenzamide may have implications in the development of new medications due to its distinct structural features. Its ability to be modified and incorporated into diverse chemical frameworks positions it as a promising scaffold for the creation of novel drug candidates with potential therapeutic benefits.
Used in Chemical Processes:
2-fluoro-N-hydroxybenzamide's unique structure and reactivity also make it suitable for use in various chemical processes. It can be employed to improve the efficiency of chemical reactions, develop new synthetic routes, and enhance the properties of existing materials.

Upstream product

• 394-35-4 methyl 2-fluorobenzoate 
• 393-52-2 2-Fluorobenzoyl chloride 
• 445-29-4 o-fluoro-benzoic acid 

Downstream Products

• 824-48-6 N-(2-fluorophenyl)formamide 
• 18595-84-1 2-(2-fluorophenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 391-07-1 2-(2-fluorophenyl)-5-phenyloxazole 

Relevant academic research and scientific papers

A new method for preparing N-acyloxaziridines via tandem O, N-addition of hydroxamic acids to methyl propiolate.

N-Acyloxaziridines were prepared from a tandem O, N-addition of hydroxamic acids to metyl propiolate in the presence of 4-methyl morpholine as a catalyst in good to excellent yields.

Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.

Rhodium(III)-catalyzed C4-amidation of indole-oximes with dioxazolones: Via C-H activation

A novel method for the Rh(III)-catalyzed oxime-directed C-H amidation of indoles with dioxazolones has been developed. This strategy provides an exclusive site selectivity and the directing group can be easily removed. This transformation features a wide substrate scope, good functional group tolerance and excellent yields, and may serve as a significant tool to construct structurally diverse indole derivatives for the screening of potential pharmaceuticals in the future. This journal is

Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions

The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.

Synthesis of 2,5-disubstituted oxazoles: Via cobalt(III)-catalyzed cross-coupling of N -pivaloyloxyamides and alkynes

An efficient synthesis of 2,5-disubstituted oxazoles via Co(iii) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.

Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones

An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.

Benzohydroxamic acids as potent and selective anti-HCV agents

A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV.

HISTONE DEACETYLASE INHIBITORS AND METHODS OF USE THEREOF

The present invention provides novel compounds for inhibiting histone deacetylases, and pharmaceutically acceptable salts and derivatives thereof. The present invention further provides methods for treating disorders regulated by histone deacetylase activity (e.g., proliferative diseases, cancer, inflammatory diseases, protozoal infections, hair loss, etc.) comprising administering a therapeutically effective amount of a compound of the invention to a subject in need thereof. The present invention also provides methods for preparing compounds of the invention.