209852-81-3

Upstream product

• 21948-76-5 (+/-)-4-(methylsulfinyl)pyridine 
• 22581-72-2 4-methylthiopyridine 
• 125556-98-1 2-(Pyridine-4-sulfinyl)-pyridine 1-oxide 
• 74-88-4 methyl iodide 

Downstream Products

• 22581-72-2 4-methylthiopyridine 
• 33399-46-1 4-ethoxypyridine 

Relevant academic research and scientific papers

Supramolecular Activation of Hydrogen Peroxide in the Selective Sulfoxidation of Thioethers by a Self-Assembled Hexameric Capsule

An efficient metal-free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by

Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases

Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright

Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum

It has been shown previously that the vanadium bromoperoxidase from Ascophyllum nodosum mediates the production of (R)-methyl phenyl sulfoxide with 91% enantiomeric excess from the corresponding sulfide in the presence of hydrogen peroxide. Investigation

Biotransformation of organic sulfides. Part 12. Conversion of heterocyclic sulfides to chiral sulfoxides by Helminthosporium sp. NRRL 4671 and Mortierella isabellina ATCC 42613

The enantioselective oxidation of a series of heterocyclic prochiral sulfides to chiral sulfoxides has been examined using the fungal biocatalysts Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613. Methylthiofuranyl and -thiophenyl

Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides

A series of alkyl aryl sulfides were metabolised, using selected strains of the soil bacterium Pseudomonas putida containing either toluene dioxygenase (TDO) or naphthalene dioxygenase (NDO), to give chiral sulfoxides. Alkyl aryl sulfoxides 2a-2k, 4a-4j and 4l, having enantiomeric excess (ee) values of >90%, were obtained by use of the appropriate strain of P. putida (UV4 or NCIMB 8859). Enantiocomplementarity was observed for the formation of sulfoxides 2a, 2b, 2d, 2j, 4a, 4b and 4d, with TDO-catalysed (UV4) oxidation favouring the (R) enantiomer and NDO-catalysed oxidation (NCIMB 8859) the (S) enantiomer. Evidence of involvement of the TDO enzyme was obtained using a recombinant strain of Escherichia coli (pKST 11). The marked degree of stereoselectivity appears to be mainly due to enzyme-catalysed asymmetric sulfoxidation, however the possibility of a minor contribution from kinetic resolution, in some cases, cannot be excluded.

Generation of Sulfenate Salts via Ipso-substitution of Azaheterocyclic Sulfoxides. First Preparation and Characterization of Sodium 2-Pyridinesulfenate

2-Alkyl- or 2-aryl-sulfinylpyridine N-oxides undergo ipsosubstitution reaction with sodium ethoxide to afford sodium sulfenates which were converted soon to the corresponding sulfinates upon contact with oxygen.Sodium 2-pyridinesulfenate was prepared and characterized by FT-IR as the first example of stable sulfenate.

An Efficient Asymmetric Oxidation of Sulfides to Sulfoxides

The Sharpless reagent for asymmetric epoxidation was modified by addition of 1 mol equiv of H2O to give a new homogenous reagent (Ti(O-i-Pr)4/diethyl tartrate/H2O/t-BuOOH = 1:2:1:1).This reagent cleanly oxidizes prochiral functionalized sulfides into optically active sulfoxides.The observed ee mainly ranged between 75 and 90percent for alkyl aryl sulfoxides and 50-71percent for dialkyl sulfoxides.A strong temperature dependence on ee was also observed in the asymmetric oxidation of methyl p-tolyl sulfoxide.

ipso-Substitution of a Sulphinyl or Sulphonyl Group Attached to Pyridine Rings and its Application for the Synthesis of Macrocycles

A sulphinyl or sulphonyl group directly bound to the 2- or 4-position of a pyridine ring was readily displaced by several nucleophiles such as RO-, RS-, and CN- to afford the corresponding ipso-substitution products.Similarly, 2-halogeno-6-methylsulphinyl- or -methylsulphonyl-pyridines also react with nuclephiles to afford 2-halogeno-6-substituted pyridine derivatives.Thus, the leaving abilities of the leaving groups fall in the order RSO2 > RSO > Br ca.Cl >> RS (R = alkyl or benzyl).The ipso-substitution can be applied to the synthesis of 2,6-disubstituted pyridino macrocycles containing both carbon-oxygen and carbon-sulphur bridges, resulting in several new macrocycles in moderate yields.