4006-79-5

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 3717-33-7 (Z)-3-chlorobenzaldehyde oxime 
• 587-04-2 m-Chlorobenzaldehyde 
• 2972-73-8 2-(3-chlorobenzylidene)malononitrile 
• 96-29-7 ethyl methyl ketone oxime 
• 873-63-2 m-chlorobenzyl alcohol 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 3717-33-7 (Z)-3-chlorobenzaldehyde oxime 
• 141891-20-5 3-Chloro-benzaldehyde O-ethyl-oxime 
• 29203-59-6 (Z)-3-chloro-N-hydroxybenzene-1-carbonimidoyl chloride 
• 141891-32-9 [1-(3-Chloro-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid 
• 766-84-7 3-chloro-benzonitrile 
• 95124-66-6 5-methyl-3-(3-chlorophenyl)-1,2,4-oxadiazole 
• 535-80-8 3-chlorobenzoate 
• 1416561-53-9 (E)-3-chlorobenzaldehyde O-butyryl oxime 
• 141891-36-3 2-[1-(3-Chloro-phenyl)-meth-(E)-ylideneaminooxy]-butyric acid 
• 141891-34-1 2-[1-(3-Chloro-phenyl)-meth-(E)-ylideneaminooxy]-propionic acid 
• 161064-09-1 3-(3-Chloro-phenyl)-5-vinyl-4,5-dihydro-isoxazole 
• 323580-19-4 5-(3-chlorophenyl)-1-hydroxytetrazole 

Relevant academic research and scientific papers

Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: Confirmation of attractive π(C=N)···π(phenyl) interactions

The crystal structures and Hirshfeld surface analyses are reported for four aldoximes, (E)-X-C6 H4 CH=N-OH [X = 3-Cl (1), 4-F (2), 2-O2 N (3) and 4-O2 N (4)]. The strong classical O-H · · · N hydrogen bonds involving the oxime group generate C(3) chains in compound 1, in contrast to the R22 (6) dimers formed in compounds 2-4; such arrangements have been shown to be the most frequently found for oximes other than salicylaldoximes (2-hydroxybenzaldehyde oximes). In general, weaker intermolecular interactions involving the X substituents, as well as C-H · · · O and π · · · π interactions have significant effects on the supramolecular arrays generated in the aggegation. A further important interaction in compound 1, and to a lesser extent in compound 4, is a π(C=N) · · · π(phenyl) molecular stacking. A data base search has indicated that short Cg(C=N) · · · Cg(phenyl) distances, -1.

A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentanedione (DPD) and related compounds as potential modulators of bacterial quorum sensing

Resistance to antibiotics is an increasingly serious threat to global public health and its management translates to significant health care costs. The validation of new Gram-negative antibacterial targets as sources for potential new antibiotics remains a challenge for all the scientists working in this field. The interference with bacterial Quorum Sensing (QS) mechanisms represents a potentially interesting approach to control bacterial growth and pursue the next generation of antimicrobials. In this context, our research is focused on the discovery of novel compounds structurally related to (S)-4,5-dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule able to modulate bacterial QS in both Gram-negative and Gram-positive bacteria. In this study, a practical and versatile synthesis of racemic DPD is presented. Compared to previously reported syntheses, the proposed strategy is short and robust: it requires only one purification step and avoids the use of expensive or hazardous starting materials as well as the use of specific equipment. It is therefore well suited to the synthesis of derivatives for pharmaceutical research, as demonstrated by four series of novel DPD-related compounds described herein.

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts

The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.

One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers

A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective CF bond cleavage.

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction

A highly stereoselective synthesis of E-isomer of aldoximes was developed through a basecatalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95 : 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction

A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yie

Electrochemical tandem synthesis of oximes from alcohols using KNO 3 as the nitrogen source, mediated by tin microspheres in aqueous medium

Electrochemical oximation of alcohols was realized with KNO3 as the nitrogen source mediated by tin microspheres.

Bicyclic piperazines as metabotropic glutatmate receptor antagonists

The invention relates to compounds of formula I or pharmaceutically acceptable salts or solvates thereof: where Ar1, A, Hy, R1, m and n are as defined in the description. The invention also includes pharmaceutical compositions and uses of, and processes of making the compounds, as well as methods of medical treatment of mGluR5-mediated disorders.

Effect of structure in benzaldehyde oximes on the formation of aldehydes and nitriles under photoinduced electron-transfer conditions

(Chemical Equation Presented) The mechanistic aspects of the photosensitized reactions of a series of benzaldehyde oximes (1a-o) were studied by steady-state (product studies) and laser flash photolysis methods. Nanosecond laser flash photolysis studies have shown that the reaction of the oxime with triplet chloranil (3CA) proceeds via an electron-transfer mechanism provided the free energy for electron transfer (ΔGET) is favorable; typically, the oxidation potential of the oxime should be below 2.0 V. Substituted benzaldehyde oximes with oxidation potentials greater than 2.0 V quench 3CA at rates that are independent of the substituent and the oxidation potential. The most likely mechanism under these conditions is a hydrogen atom transfer mechanism as this reaction should be dependent on the O-H bond strength only, which is virtually the same for all oximes. Product studies have shown that aldoximes feact to give both the corresponding aldehyde and the nitrile. The important intermediate in the aldehyde pathway is the iminoxyl radical, which is formed via an electron transfer-proton transfer (ET-PT) sequence (for oximes with low oxidation potentials) or via a hydrogen atom transfer (HAT) pathway (for oximes with larger oxidation potentials). The nitriles are proposed to result from intermediate iminoyl radicals, which can be formed via direct hydrogen atom abstraction or via an electron-transfer-proton- transfer sequence. The experimental data seems to support the direct hydrogen atom abstraction as evidenced by the break in linearity in the plot of the quenching rates against the oxidation potential, which suggests a change in mechanism. The nitrile product is favored when electron-accepting substituents are present on the benzene ring of the benzaldehyde oximes or when the hydroxyl hydrogen atom is unavailable for abstraction. The latter is the case in pyridine-2-carboxaldoxime (2), where a strong intramolecular hydrogen bond is formed. Other molecules that form weaker intramolecular hydrogen bonds such as 2-furaldehyde oxime (3) and thiophene-2-carboxaldoxime (4) tend to yield increasing amounts of aldehyde.

Titanium oxide (TiO2) catalysed one-step Beckmann rearrangement of aldehydes and ketones in solvent free conditions

In the presence of titanium oxide (TiO2) and without any additional organic solvents, Beckmann rearrangement of several ketones and aldehydes was performed in good yield.