50342-50-2

Usage

Uses

Used in Chemical Synthesis:
2-Benzofurancarboxamide(7CI,9CI) is used as a building block in the synthesis of various organic compounds. Its unique structure and functional groups make it a valuable component in the creation of complex molecules for different applications.
Used in Research:
In the field of research, 2-Benzofurancarboxamide(7CI,9CI) serves as a key compound for studying the properties and reactions of benzofuran derivatives. It aids in understanding the reactivity, stability, and potential applications of related chemical structures.
Used in Pharmaceutical Development:
Due to its structural and functional properties, 2-Benzofurancarboxamide(7CI,9CI) may have potential pharmacological and therapeutic applications. It can be further modified or used as a precursor in the development of new drugs targeting specific medical conditions.
Used in Solvent Systems:
2-Benzofurancarboxamide(7CI,9CI) is known to exhibit moderate solubility in certain organic solvents. This property can be utilized in solvent systems for various chemical processes, including extraction, purification, and reaction media.
Used in Chemical Stability Studies:
The stability of 2-Benzofurancarboxamide under specific temperature and pH conditions makes it suitable for studies on chemical stability. It can be used to investigate the effects of environmental factors on the integrity and reactivity of chemical compounds.

InChI:InChI=1S/C9H7NO2/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5H,(H2,10,11)

Upstream product

• 41717-28-6 2-benzofuroyl chloride 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 79-37-8 oxalyl dichloride 
• 7169-37-1 7-methoxy-3-benzofuranone 
• 3199-61-9 ethyl coumarilate 
• 90-02-8 salicylaldehyde 
• 79-07-2 Chloroacetamide 
• 872-85-5 pyridine-4-carbaldehyde 
• 91703-34-3 2-(β,β-dibromovinyl)phenol 
• 13939-06-5 molybdenum hexacarbonyl 
• 4265-16-1 2-formylbenzo[b]furan 
• 125418-83-9 2-(2-formylphenoxy)acetonitrile 
• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 68838-62-0 bromo-malonic acid ethyl ester-amide 

Downstream Products

• 37798-05-3 benzofuran-2-ylmethanamine 

Relevant academic research and scientific papers

Ruthenium-catalyzed cascade C-H activation/annulation of: N -alkoxybenzamides: Reaction development and mechanistic insight

A highly selective ruthenium-catalyzed C-H activation/annulation of alkyne-tethered N-alkoxybenzamides has been developed. In this reaction, diverse products from inverse annulation can be obtained in moderate to good yields with high functional group compatibility. Insightful experimental and theoretical studies indicate that the reaction to the inverse annulation follows the Ru(ii)-Ru(iv)-Ru(ii) pathway involving N-O bond cleavage prior to alkyne insertion. This is highly different compared to the conventional mechanism of transition metal-catalyzed C-H activation/annulation with alkynes, involving alkyne insertion prior to N-O bond cleavage. Via this pathway, the in situ generated acetic acid from the N-H/C-H activation step facilitates the N-O bond cleavage to give the Ru-nitrene species. Besides the conventional mechanism forming the products via standard annulation, an alternative and novel Ru(ii)-Ru(iv)-Ru(ii) mechanism featuring N-O cleavage preceding alkyne insertion has been proposed, affording a new understanding of transition metal-catalyzed C-H activation/annulation.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides

A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

Method for preparing benzofuran-2-carboxamide compound

The invention discloses a method for preparing a benzofuran-2-carboxamide compound. The method comprises the following steps: sequentially adding an alkali and a 2-formylaryloxy acetonitrile derivative into a solvent, and carrying out a reaction at a certain temperature to obtain a reaction solution after complete reaction; and sequentially subjecting the reaction solution to extraction, drying, concentration and column chromatographic separation to obtain a target product, i.e., the benzofuran-2-carboxamide compound. According to the invention, common cheap easily-available inorganic base ororganic base is used as a catalyst of the reaction, no metal or organic catalyst is used, and no additive is needed; reaction conditions are mild; product yield is high; operation is simple; and the method is environment-friendly. Reagents and the catalyst used in the method are rich in industrial sources and easy to obtain, so production cost is low; product purity is high; and the method has good industrial application prospects.

Tandem Synthesis of 2-Carboxybenzofurans via Sequential Cu-Catalyzed C-O Coupling and Mo(CO)6-Mediated Carbonylation Reactions

A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C-O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free conditions.

Pyridine-Enabled C-N Bond Activation for the Rapid Construction of Amides and 4-Pyridylglyoxamides by Cooperative Palladium/Copper Catalysis

A pyridine-enabled C-N bond activation of peptidomimetics employing cooperative palladium/copper catalysis in water is developed. Diverse amides and 4-pyridylglyoxamides are simultaneously synthesized through two steps from commercially available materials in a rapid, environmentally friendly, and high atom-economical manner.

A systematic exploration of the effects of flexibility and basicity on sigma (σ) receptor binding in a series of substituted diamines

The sigma-1 receptor (S1R) has attracted a great deal of attention as a prospective drug target due to its involvement in numerous neurological disorders and, more recently, for its therapeutic potential in neuropathic pain. As there was no crystal structure of this membrane-bound protein reported until 2016, ligand generation was driven by pharmacophore refinements to the general model suggested by Glennon and co-workers. The generalised S1R pharmacophore comprises a central region where a basic amino group is preferred, flanked by two hydrophobic groups. Guided by this pharmacophore, S1R ligands containing piperazines, piperazinones, and ethylenediamines have been developed. In the current work, we systematically deconstructed the piperazine core of a prototypic piperazine S1R ligand (vide infra) developed in our laboratories. Although we did not improve the affinity at the S1R compared to the lead, we identified several features important for affinity and selectivity. These included at least one basic nitrogen atom, conformational flexibility and, for S1R, a secondary or tertiary amine group proximal to the anisole. Furthermore, S2R selectivity can be tailored with functional group modifications of the N-atom proximal to the anisole.

TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols

An interesting and convenient procedure for the oxidative transformation of acetophenones and carbinols to primary benzamides has been developed. By using tetra-n-butylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, the desired benzamides were isolated in moderate to good yields in aqueous solution. Notably, not only acetophenones but also propiophenones can be applied as substrates as well. Hence, we believe that this new procedure is not just a catalytic version of the iodine-based method. the Partner Organisations 2014.