10354-47-9

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 108-91-8 cyclohexylamine 
• 58777-49-4 2-furoyl bromide 
• 54829-48-0 2-iodofuran 
• 201230-82-2 carbon monoxide 
• 609-38-1 furan-2-carboxylic acid amide 
• 626-62-0 Cyclohexyl iodide 
• 88-14-2 2-furanoic acid 
• 144223-33-6 2-furoyl-1H-1,2,3-benzotriazole 

Downstream Products

• 126265-85-8 N-cyclohexylfuran-2-carbothioamide 
• 876893-30-0 N-[(1H-1,2,3-benzotriazol-1-yl)(2-furyl)methylidene]-N-cyclohexylamine 
• 220717-32-8 N-Cyclohexyl-5-carbamoylfuran-2-sulfonic Acid Sodium Salt 

Relevant academic research and scientific papers

Integration of co2 reduction with subsequent carbonylation: Towards extending chemical utilization of co2

Currently, it still remains a challenge to amplify the spectrum of chemical fixation of CO2, although enormous progress has been achieved in this field. In view of the widespread applications of CO in a myriad of industrial carbonylation processes, an alternative strategy is proposed in which CO2 reduction to CO is combined with carbonylation with CO generated ex situ, which affords efficiently pharmaceutically and agrochemically attractive molecules. As such, CO2 in this study was efficiently reduced by triphenysilane using CsF to CO in a sealed two-chamber reactor. Subsequently, palladium-catalyzed aminocar-bonylation, carbonylative Sonogashira coupling of aryl iodides, and rhodium(I)-mediated Pauson–Khand-type reaction proceeded smoothly to yield amides, alkynones, and bicyclic cy-clopentenones, respectively. Furthermore, the formed alkynones can further be successfully converted to a series of heterocycles, for example, pyrazoles, 3a-hydroxyisoxazolo[3,2-a]isoindol-8-(3aH)-one derivatives and pyrimidines in moderate yields. The striking features of this protocol include operational simplicity, high efficiency, and relatively broad application scope, which represents an alternative avenue for CO2 transformation.

Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature

The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.

A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions

Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.

Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles

Microwave reactions of primary and secondary amines with imidoylbenzotriazoles 6a-w gave diversely substituted amidines 7a-Aa in 76-94% yields. Convenient preparations of a variety of amides 5a-Ab (87-96%) and imidoylbenzotriazoles 6a-w (56-95%) have also been developed using microwave irradiation under mild conditions and short reaction times. These results demonstrate further the advantages of microwave synthesis and introduce a new application of imidoylbenzotriazoles in the preparation of polysubstituted amidines.

Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their anilides

A series of m- and p-substituted anilides of benzoic acid, 2-thienoic acid, and 2-furoic acid were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shifts of proton and carbon signals of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzanilides against those of the 2-thienamides and 2-furamides gave an excellent correlation and the values of the slopes are 0.79 and 0.52, respectively, in dimethyl sulfoxide-d6. The slopes could be considered as a set of aromaticity index.

Facile Conversions of Carboxylic Acids into Amides, Esters, and Thioesters Using 1,1'-Oxalyldiimidazole and 1,1'-Oxalyldi(1,2,4-triazole)

Aliphatic, aromatic, and heteroaromatic carboxylic acids react with 1,1'-oxalyldiimidazole (1) or 1,1'-oxalyldi(1,2,4-triazole) (2) in acetonitrile for 40 min at 40 degC to give the corresponding 1-acylazole intermediates (11), which promptly undergo aminolysis and alcoholysis to form amides (13) including dipeptides (14), esters (16), and thioesters (19).These findings show that both 1 and 2 can be utilized as condensing reagents for the synthesis of carboxylic acid derivatives.Keywords --- 1,1'-oxalyldiimidazole; 1,1'-oxalyldi(1,2,4-triazole); 1,1'-carbonyldiimidazole; 1-acylazole; condensing reagent; amidation; esterification; dipeptide; aminolysis; alcoholysis