57666-50-9

Upstream product

• 13803-39-9 5-phenylfuran-2-carbaldehyde 
• 63191-69-5 5-phenyl-furan-2-carbaldehyde oxime 
• 13803-16-2 5-phenylfuran-2-carboxaldehyde oxime 
• 17113-33-6 2-phenylfuran 
• 506-68-3 bromocyane 
• 67-56-1 methanol 

Downstream Products

• 60838-09-7 5-(5-phenyl-furan-2-yl)-1⁽²⁾H-tetrazole 
• 350691-65-5 N²-Phenyl-5-phenylfuran-2-carboximidamide 
• 350692-01-2 N¹-Acetyl-N¹-(5-phenyl-2-furyl)-N²-phenylurea 
• 59589-50-3 O-methyl-5-phenyl-2-furamidoxime 
• 62821-37-8 2-(5-phenyl-furan-2-yl)imidazole hydrochloride 

Relevant academic research and scientific papers

Alkali α-MnO2/Na: XMnO2 collaboratively catalyzed ammoxidation-Pinner tandem reaction of aldehydes

The tandem reaction is a growing field to yield important advances toward green and sustainable chemistry. Herein, we report a bifunctional manganese oxide catalyst with an interface binding redox phase (α-MnO2) and a basic phase (NaxMnO2). The molar ratio of NaOH/Mn plays a great role in the formation of α-MnO2/NaxMnO2. The sodium cation is essential for the formation of a basic NaxMnO2 phase while the potassium cation promotes the formation of a redox-active α-MnO2 phase. The interface structure of α-MnO2/NaxMnO2 geometrically favors the ammoxidation-Pinner tandem reaction to synthesize imidates in a 58-96% yield from aldehydes. Thus a phase collaborative effect is observed. In the ammoxidation process, the redox cycle of MnIV/MnIII is involved and the lattice oxygen in the α-MnO2 phase acts as an active oxygen species. The O-H in methanol is activated and dissociated on the basic sites of NaxMnO2 to the adsorbed methoxyl species to facilitate the Pinner synthesis. This approach bypasses the conventional synthesis of imidates, which suffer from harsh reaction conditions and the requirement for multiple steps.

Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C-H bonds

A gallium-catalysed, direct cyanation reaction of aromatic and heteroaromatic C-H bonds with cyanogen bromide was developed as a practical synthetic method for the preparation of aromatic nitriles. The Royal Society of Chemistry 2012.

A simple method for the synthesis of 5-substituted 2-cyanofurans

A new method based on the Schmidt reaction was developed for the production of 5-R-2-cyanofurans from 5-R-furfurals.

One-step synthesis of 5-acylisothiazoles from furans

Premixed ethyl carbamate, thionyl chloride and pyridine (which generate thiazyl chloride, N≡SCl) in boiling benzene or toluene convert 2,5- and 2,3,5-substituted furans into 5-acylisothiazoles regiospecifically. The reactions are much faster and generally higher yielding in boiling chlorobenzene with more thionyl chloride and with pyridine or isoquinoline as base. Under the more vigorous conditions, even fully substituted 3-bromofurans give isothiazoles, with the displacement of bromine. Deactivated furans, with electron-withdrawing groups such as ester, cyano, benzoyl and phenylsulfonyl in the α-position, react under the more vigorous conditions to give 5-acylisothiazoles with the electronegative group in the 3-position. The 'activated' 2-methyl-5-phenyl- and 5-phenyl-2-phenylthio-furans react analogously, with the more electron-releasing group becoming part of the 5-acyl substituent, exclusively or predominantly. These results are explained by initial electrophilic attack of the furan ring to give a β-thiazyl derivative which spontaneously ring-opens and closes to the isothiazole. The X-ray structures of five of the differently substituted isothiazole compounds are reported. All have very similar patterns of bonding within their isothiazole rings that appear to be independent of the electron-withdrawing or -donating nature of the substituents. Three of the compounds (8a, 8g and 13) have loosely linked chain structures in the solid state, adjacent molecules being connected by combinations of hydrogen bonding and π-π stacking interactions.

SYNTHESIS OF 5-SUBSTITUTED CYANOFURANS AND THEIR REACTION WITH HYDRAZINE

Based on the Schmidt reaction, a new method has been developed for the preparation of nitriles in furan series from the corresponding furfural derivatives.Depending on conditions, the reaction of 5-substituted cyanofurans with hydrazine leads to amidrazones, N-aminotriazoles, or 1,2,4,5-dihydrotetrazines.

5-Phenyl-2-furamidines: A new chemical class of potential antidepressants

A series of 5-phenyl-2-furamidines has been synthesized and evaluated for antidepressant activities. Substitution in the phenyl ring with a nitro (4) or an amino (12) group in the ortho-position resulted in an increase in antidepressant activity. Both 4 and 12 antagonized tetrabenazine-induced ptosis in rodents and inhibited norepinephrine (noradrenaline) uptake into crude synaptosomes of whole mouse brain at doses or concentrations comparable to those of the tricyclic antidepressants. However, these compounds did not possess the anticholinergic and antihistaminic activities common to tricyclic antidepressants. In addition, they lacked monoamine oxidase inhibitory activity. The 5-phenyl-2-furamidines represent a new chemical class of antidepressants and may be useful for depressive patients who cannot tolerate the compromising side effects of the tricyclic antidepressants and monoamine oxidase inhibitors.