58416-69-6

Upstream product

• 288-13-1 NH-pyrazole 
• 103-63-9 1-phenyl-2-bromoethane 
• 153997-24-1 (Z)-1-phenyl-2-(pyrazol-1-yl)ethene 
• 536-74-3 phenylacetylene 
• 74-88-4 methyl iodide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 956723-13-0 2-phenethyl-2H-pyrazole-3-carbaldehyde 

Relevant academic research and scientific papers

Chemo-, regio-, and stereoselective n-alkenylation of pyrazoles/ benzpyrazoles using activated and unactivated alkynes

Transition-metal-free chemo-, regio-, and stereoselective synthesis of (Z) and (E) styryl pyrazoles and benzpyrazoles by the addition of N-heterocycles onto functionalized terminal and internal alkynes using a super basic solution of KOH/DMSO has been described. The stereochemical outcome of the reaction was governed by time and quantity of the base. The reaction of pyrazoles and benzpyrazoles onto alkynes takes place chemoselectively without affecting the free -NH2 group of pyrazoles and -OH group of alkynes. The designed protocol was well implemented on alkynes bearing long alkyl chain, an alicyclic ring, hydroxy, ether, and ester functionality, which offer the N-alkenylated products in good yields. This developed methodology also provides easy access for the synthesis of bis-vinylated heterocycles. The presence of free -NH2, -OH, -COOR, and halo group in styryl pyrazoles, could be further utilized for synthetic elaboration, which is advantageous for biological evaluation. For the first time, we have disclosed the base-mediated conversion of (Z)-styryl pyrazoles to (E)-styryl pyrazoles in KOH/DMSO system. The cis-rans isomerization was supported by the control experiments and deuterium labeling studies.

Ruthenium-catalyzed c-h silylation of 1-arylpyrazole derivatives and fluoride-mediated carboxylation: Use of two nitrogen atoms of the pyrazole Group

Carboxylation of 1-arylpyrazole derivatives was developed using a ruthenium-catalyzed ortho silylation in conjunction with fluoride-mediated carboxylation with carbon dioxide. The two nitrogen atoms of pyrazole play crucial roles in promoting ortho silylation via the formation of a five-membered ruthenacycle and in accelerating aryl anion formation by lowering the electron density of the aromatic ring. Georg Thieme Verlag Stuttgart New York.

Sintered silicon carbide: A new ceramic vessel material for microwave chemistry in single-mode reactors

Silicon carbide (SiC) is a strongly microwave absorbing chemically inert ceramic material that can be utilized at extremely high temperatures due to its high melting point and very low thermal expansion coefficient. Microwave irradiation induces a flow of electrons in the semiconducting ceramic that heats the material very efficiently through resistance heating mechanisms. The use of SiC carbide reaction vessels in combination with a single-mode microwave reactor provides an almost complete shielding of the contents inside from the electromagnetic field. Therefore, such experiments do not involve electromagnetic field effects on the chemistry, since the semiconducting ceramic vial effectively prevents microwave irradiation from penetrating the reaction mixture. The involvement of electromagnetic field effects (specific/nonthermal microwave effects) on 21 selected chemical transformations was evaluated by comparing the results obtained in microwave-transparent Pyrex vials with experiments performed in SiC vials at the same reaction temperature. For most of the 21 reactions, the outcome in terms of conversion/purity/product yields using the two different vial types was virtually identical, indicating that the electromagnetic field had no direct influence on the reaction pathway. Due to the high chemical resistance of SiC, reactions involving corrosive reagents can be performed without degradation of the vessel material. Examples include high-temperature fluorine-chlorine exchange reactions using triethylamine trihydrofluoride, and the hydrolysis of nitriles with aqueous potassium hydroxide. The unique combination of high microwave absorptivity, thermal conductivity, and effusivity on the one hand, and excellent temperature, pressure and corrosion resistance on the other hand, makes this material ideal for the fabrication of reaction vessels for use in microwave reactors. Simulating conductive heat transfer in a microwave: Using reaction vials made out of strongly microwave-absorbing silicon carbide (SiC) in a microwave reactor simulates a conductively heated autoclave experiment due to efficient shielding of the electromagnetic field by the SiC vial. Advantages of SiC vials for microwave processing include their excellent corrosion resistance, thermal stability, and high thermal effusivity and conductivity.

Microwave chemistry in silicon carbide reaction vials: Separating thermal from nonthermal effects

Running oil-bath chemistry in a microwave! Using reaction vials made out of strongly microwave-absorbing silicon carbide (SiC) in a microwave reactor simulates experiments conducted in an autoclave with conductive heating because of the efficient shielding of the electromagnetic field by the SiC vial. This technology makes it possible to study the significance of microwave effects.

FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE

This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. The invention also provides methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure: wherein A is NH or S. Q is a member selected from CR1 and N. X and Y are members independently selected from O, S, CR2, N and NH. R1, R2 and R4 are members independently selected from H and F, provided that at least one member selected from R1, R2 and R4 is F. R6 is a member selected from O?X+ and OH, wherein X+ is a positive ion, which is a member selected from inorganic positive ions and organic positive ions.

Silicon carbide passive heating elements in microwave-assisted organic synthesis

Microwave-assisted organic synthesis in nonpolar solvents is investigated utilizing cylinders of sintered silicon carbide (SiC)-a chemically inert and strongly microwave absorbing material-as passive heating elements (PHEs). These heating inserts absorb microwave energy and subsequently transfer the generated thermal energy via conduction phenomena to the reaction mixture. The use of passive heating elements allows otherwise microwave transparent or poorly absorbing solvents such as hexane, carbon tetrachloride, tetrahydrofuran, dioxane, or toluene to be effectively heated to temperatures far above their boiling points (200-250 °C) under sealed vessel microwave conditions. This opens up the possibility to perform microwave synthesis in unpolar solvent environments as demonstrated successfully for several organic transformations, such as Claisen rearrangements, Diels-Alder reactions, Michael additions, N-alkylations, and Dimroth rearrangements. This noninvasive technique is a particularly valuable tool in cases where other options to increase the microwave absorbance of the reaction medium, such as the addition of ionic liquids as heating aids, are not feasible due to an incompatibility of the ionic liquid with a particular substrate. The SiC heating elements are thermally and chemically resistant to 1500 °C and compatible with any solvent or reagent.

Alkylation and arylation of pyrazoles under solvent-free conditions: Conventional heating versus microwave irradiation

The use of sodium hydrogen carbonate under solvent-free conditions and microwave irradiation is by far the best method for N-alkylating pyrazoles. The yields are good and the method is devoid of side reactions (quaternization, isomerization, hydrogen hali