609-35-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Furanecarboxamide is used as a building block for the synthesis of various drugs, contributing to the development of new pharmaceutical compounds. Its presence in drug synthesis facilitates the creation of a diverse range of medicinal agents.
Used in Agrochemical Production:
In the agrochemical industry, 3-furanecarboxamide is utilized in the production of various agrochemicals, playing a crucial role in the development of products that enhance crop protection and yield.
Used in Flavors and Fragrances Industry:
3-Furanecarboxamide is employed as a precursor in the synthesis of flavors and fragrances, adding to the complexity and variety of scents and tastes in the market.
Used as a Reagent in Chemical Reactions:
3-Furanecarboxamide serves as a reagent in various chemical reactions, enabling the synthesis of other functionalized compounds and contributing to the advancement of organic chemistry.
Used as a Precursor to Other Functionalized Compounds:
It acts as a precursor, allowing for the development of other functionalized compounds that can be used in different industries, showcasing its versatility in chemical synthesis.
Used as a Ligand in Coordination Chemistry:
3-Furanecarboxamide can also function as a ligand in coordination chemistry, playing a role in the formation of coordination compounds and contributing to the field of inorganic chemistry.
With potential applications in the development of new materials and technologies, 3-furanecarboxamide is a key component in the advancement of various scientific and industrial fields.

Upstream product

• 26214-65-3 furan-3-carbonyl chloride 
• 743420-66-8 2,2,2-trichloro-1-(furan-3-yl)ethan-1-one 
• 83124-80-5 3-trichloroacetyl-4,5-dihydrofuran 
• 1336-21-6 ammonium hydroxide 
• 71-36-3 butan-1-ol 
• 498-60-2 furan-3-carboxaldehyde 
• 30078-65-0 3-furylnitrile 
• 488-93-7 3-Furoic acid 

Downstream Products

• 4543-47-9 3-furylmethylamine 
• 1017039-36-9 C₁₃H₁₁NO₃ 
• 52109-89-4 N-(3-methoxyphenyl)furan-3-carboxamide 
• 30078-65-0 3-furylnitrile 

Relevant academic research and scientific papers

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst

Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile.

Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus

Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.

Phosphinous Acid-Assisted Hydration of Nitriles: Understanding the Controversial Reactivity of Osmium and Ruthenium Catalysts

The synthesis and catalytic behavior of the osmium(II) complexes [OsCl2(η6-p-cymene)(PR2OH)] [R=Me (2 a), Ph (2 b), OMe (2 c), OPh (2 d)] in nitrile hydration reactions is presented. Among them, the best catalytic results were obtained with the phosphinous acid derivative [OsCl2(η6-p-cymene)(PMe2OH)] (2 a), which selectively provided the desired primary amides in excellent yields and short times at 80 °C, employing directly water as solvent, and without the assistance of any basic additive (TOF values up to 200 h?1). The process was successful with aromatic, heteroaromatic, aliphatic, and α,β-unsaturated organonitriles, and showed a high functional group tolerance. Indeed, complex 2 a represents the most active and versatile osmium-based catalyst for the hydration of nitriles reported so far in the literature. In addition, it exhibits a catalytic performance similar to that of its ruthenium analogue [RuCl2(η6-p-cymene)(PMe2OH)] (4). However, when compared to 4, the osmium complex 2 a turned out to be faster in the hydration of less-reactive aliphatic nitriles, whereas the opposite trend was generally observed with aromatic substrates. DFT calculations suggest that these differences in reactivity are mainly related to the ring strain associated with the key intermediate in the catalytic cycle, that is, a five-membered metallacyclic species generated by intramolecular addition of the hydroxyl group of the phosphinous acid ligand to the metal-coordinated nitrile.

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

Hexagonal Mesoporous Silica-Supported Copper Oxide (CuO/HMS) Catalyst: Synthesis of Primary Amides from Aldehydes in Aqueous Medium

Hexagonal mesoporous silica (HMS)-supported copper oxides (CuO/HMS) have been prepared by a sol–gel method and characterized by X-ray diffraction, FTIR spectroscopy, transmission electron microscopy, N2 sorption, inductively coupled plasma (ICP), X-ray photoelectron spectroscopy (XPS), H2 temperature-programed reduction (TPR), NH3 temperature-programed desorption (TPD), and high-resolution (HR)-TEM techniques. An analysis of these results revealed a mesoporous material system with a high surface area (974 m2 g?1) and uniform pore-size distribution. The catalytic efficacy of CuO on the HMS support with varying Cu loadings (1, 3, 5, 10, and 15 wt %) was investigated for the transformation of aldehydes to primary amides; 3 wt % CuO/HMS exhibited good catalytic performance with good to excellent yields of amides (60–92 %) in benign aqueous medium. The intrinsically heterogeneous catalyst could be recovered after the reaction and reused without any noticeable loss in activity.

Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions

Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.

Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones

Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.

Exploring rhodium(I) complexes [RhCl(COD)(PR3)] (COD = 1,5-cyclooctadiene) as catalysts for nitrile hydration reactions in water: The aminophosphines make the difference

Several rhodium(I) complexes, [RhCl(COD)(PR3)], containing potentially cooperative phosphine ligands, have been synthesized and evaluated as catalysts for the selective hydration of organonitriles into amides in water. Among the different phosphines screened, those of general composition P(NR 2)3 led to the best results. In particular, complex [RhCl(COD){P(NMe2)3}] was able to promote the selective hydration of a large range of nitriles in water without the assistance of any additive, showing a particularly high activity with heteroaromatic and heteroaliphatic substrates. Employing this catalyst, the antiepileptic drug rufinamide was synthesized in high yield by hydration of 4-cyano-1-(2,6- difluorobenzyl)-1H-1,2,3-triazole. For this particular transformation, complex [RhCl(COD){P(NMe2)3}] resulted more effective than related ruthenium catalysts.

An efficient ruthenium(iv) catalyst for the selective hydration of nitriles to amides in water under mild conditions

A Ru(iv) catalyst able to promote the selective hydration of nitriles to amides in water, at low metal loadings and under mild conditions, is presented. This journal is the Partner Organisations 2014.