69212-36-8

Usage

Structure

Pyridine derivative with two methylthio (CH3S) groups attached at positions 2 and 3 of the pyridine ring

Usage

Building block in organic synthesis, starting material for the synthesis of various pharmaceuticals and agrochemicals

Physical properties

Volatile and flammable liquid, strong odor

Potential applications

Fragrances and flavors, antimicrobial properties

Industrial interest

Use as a chemical intermediate in various industrial processes

InChI:InChI=1/C7H9NS2/c1-9-6-4-3-5-8-7(6)10-2/h3-5H,1-2H3

Upstream product

• 2402-77-9 2,3-dichloro-pyridine 
• 5188-07-8 sodium thiomethoxide 
• 98627-05-5 2,3-bis(isopropylthio)pyridine 
• 74-88-4 methyl iodide 
• 88912-24-7 5,6-dichloro-2-pyridinecarboxylic acid 
• 109-09-1 2-chloropyridine 
• 624-92-0 Dimethyldisulphide 
• 372-48-5 2-fluoropyridine 
• 66715-65-9 pyridine-2-sulfonyl chloride 
• 106762-43-0 Piperidin-1-yl pyridin-2-yl sulfone 
• 700873-86-5 2-methoxy-5,6-bis-methylsulfanyl-2,3-dihydro-pyridine 
• 91164-62-4 5,6-bis-methylpyridine-2-carboxylic acid 

Relevant academic research and scientific papers

Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functiona

One-pot double functionalisation of π-deficient heterocyclic lithium reagents

Herein, we report an efficient method for the double functionalisation of lithiated halogenopyridines, -pyrazines or -furopyridines through a convenient one-pot electrophilic trapping/nucleophilic substitution sequence.

Synthesis and easy aromatisation of 5-substituted 6-(alkylthio)-2-methoxy-2,3-dihydropyridines. A new approach to the pyridine ring

Reaction of lithiated methoxyallene, 1-ethoxyethoxyallene, 1-(methylthio)propyne and 2-butyne with methoxymethyl isothiocyanate, MeOCH2N=C=S followed by methylation affords the imidothioates H2C=C=C(R)C(SMe)=NCH2OMe [R=Me, OMe, OCH(Me)OEt, SMe]. Rearrangement to the fully conjugated systems H2C=CH-C(R)=C(SMe)-N=CHOMe and subsequent electrocyclisation of these compounds leads to the 5-substituted 6-(methylthio)-2-methoxy-2,3-dihydropyridines with good to excellent yields. In the presence of acidic catalysts or by heating at elevated temperatures these dihydropyridines eliminate methanol to afford 3-substituted 2-(methylthio)pyridines. The aroma compound 2-(methylthio)-3-pyridinol was obtained by acid-catalysed treatment of 3-(1-ethoxyethoxy)-2-(methylthio)pyridine.

2,5-bis alkyl sulfonyl and 2,5-bis alkyl thio substituted-pyridines

A process for preparing substituted-pyridines having a sulfonyl type substituted at the 3 or 5 position of the pyridine ring and a phenoxy type substituent at the 2 position is described.

NEW REACTIONS OF PYRIDINES AND TOTAL SYNTHESIS OF THE FUNGAL TOXIN ORELLANINE

Dihalogenated pyridines react easily with sulphur nucleophiles, in dipolar aprotic solvents (DMF), to afford the products of mono- or of bis-substitution depending on the experimental conditions.On the contrary, with oxygen nucleophiles the bis-substituted products can be obtained only with some particular substrates.A new and efficient procedure to effect the homo-coupling of halogenoarenes will be presented.This reaction, wich occurs under the influence of low-valent nickel complexes, allowed us to effect the total synthesis of Orellanine, the lethal toxin of Cortinarius orellanus mushroom, as well as the syntheses of its decompositionproducts Orellinine and Orelline.The chemical properties of these three products and their behaviour towards UV irradiation will be presented and discussed.

THE REACTIONS OF SOME HALOGENATED PYRIDINES WITH METHOXYDE AND METHANETHIOLATE IONS IN DIMETHYLFORMAMIDE

The reactions of 2,6- and 2,5-dibromopyridines and of 2,3- and 3,5-dichloropyridines with sodium isopropanethiolate and methanethiolate afforded the products of mono- or of bis-substitution depending on the experimental conditions.The same pyridines reacted with sodium methoxide to give good yields of the mono-substituted products; bis-substitution occurred easily only in the case of the 2,6-dibromo- and of the 3,5-dichloropyridine.The syntheses of some methoxy thiomethoxypyridine, starting from the halogeno methoxypyridines or from the halogeno thiomethoxypyridines are also described.The bis-(alkylthio)pyridines can be fragmented by sodium in HMPA to give the bis(mercapto)pyridines.

bis-Alkylsulfonylpyridines

Dihalogenated pyridines, some activated with carboxylic, ester or cyano group, were allowed to react with sodium alkylmercaptides.After hydrolysis of the ester or cyano group followed by decarboxylation, bis-alkylthiopyridines with substituents at 2,3-, 2,4-, 2,5-, 2,6- and 3,5-positions were prepared.These compounds were oxidized to bis-alkylsulfonylpyridines.